Chiral inheritance effect in the reactive cystine-based coassembly system

Domain: chemistry
Published: 2026-02-24
Editorial outcome: minor_revision

Abstract
Controlled chemical reactions in the condensed state are key steps in designing smart materials. Due to the absence of diffusion and sufficient molecular collision, the reaction efficiency in the solid or aggregated state is expectedly much lower than the solution phase. Herein we report the templating effects in self-assemblies undergoing multiple reactions using an aromatic cystine derivative. Disulfide bond cleavage into cysteine triggered by a reductant is quantitative in aggregates, leading to the molecular rearrangement. Coassembled with a guest pentafluoropyridine through π-hole/π interaction allows for a cascade two-step reaction including reduction and aromatic nucleophilic substitution. These reactions in the condensed, self-assembled state are efficient with significant impacts on the structures of nanoarchitectures. Interestingly, the chiral expression at macroscopic scale and corresponding chiroptical activities exhibit templating and inheritance effect thanks to the sacrificial templating role of pristine aggregates. We introduce new type efficient reactions in the self-assembled states, realizing flexible control by introducing guest, and unveil the chiral inheritance effect in topochemical evolutions.

Introduction
Materials composed of molecular units with intrinsic responsiveness can undergo reversible changes in chemical structure or molecular conformation upon exposure to external stimuli such as light, heat, electric field, pH, or chemicals1–6. These transformations can further induce macroscopic changes in color, morphology, swelling, conductivity, and luminescence7–13. Molecular and supramolecular systems are primarily engineered to respond to such stimuli, most of which rely on reversible non-covalent interactions under kinetic control, such as rapid interfacial adsorption14–19. However, stimuli-responsive materials governed by chemical reactions, particularly those operating under spatial confinement such as in the solid state, remain a significantly underexplored area. Their importance lies in the ability of such constrained environments to direct supramolecular assembly through spatial restrictions, thereby enabling unique chiroptical properties. In contrast to previously reported chiral nanostructures, these in situ transformation systems, prepared via a post-assembly reaction approach, exhibit a strong templating effect and promising potential for applications in adaptive optical devices, chiroptical switches, and smart sensors. Nonetheless, limitations such as slow response kinetics, limited recyclability, and challenges in precisely controlling and determining the exact molecular self-assembly patterns under confinement still need to be addressed.

There are limitations in reaction efficiency under confinement, within self-assembled phases, or in solid-state systems20–22. Unlike solution-phase systems, reactions under confinement or in the solid state occur in highly restricted physicochemical environments, where molecular mobility and mass transport are significantly limited23–26. Such spatial confinement can unlock exceptional potential for enhancing reaction activity, controlling pathways, and improving product selectivity27–30. The organization of molecules (such as in crystalline state), interfacial migration, and restricted diffusion—along with steric confinement, solvation exclusion, and orientational effects—can significantly regulate reaction mechanisms, suppress side reactions, and enhance regio- and stereoselectivity31–34. The fixed conformation of reactants in the solid/confined state may facilitate precise control over reaction sites and modes, and may allow stabilization of otherwise transient intermediates or inaccessible phases in solution35–37. Despite these advantages, the scope of solid-state reactions remains limited, largely due to restricted molecular mobility, hindered diffusion, and challenges in establishing catalytic cycles38–40. Many reactions have been successfully implemented in confined or solid phases, including [2+2] and [4+2] photocycloadditions, click reactions, boronic ester formation, and imine condensations41,42. These transformations generally proceed under catalyst-free and mild conditions, without the need for harsh thermal or cryogenic environments. Nonetheless, it remains an open question as to how many of the diverse covalent transformations developed by synthetic chemists can be adapted to confined systems. This underscores a rich landscape of chemical questions and properties worthy of in-depth investigation43,44. The development of dynamic covalent reactions for constructing responsive materials presents major challenges, particularly in the exploration of efficient chemical reactions.

Expanding the scope of such reactions from traditional crystalline systems to soft-matter or mesoscopic assembled phases is essential for enabling functionalities and applications45. For instance, dynamic chemical reactions in assembled molecular states are also critical to achieving supramolecular chirality evolution and the design of intelligent chiral materials46. Supramolecular chirality offers tunable, reversible, and stimuli-responsive characteristics, which can evolve through several mechanisms: chiral induction, chirality transfer and amplification during cooperative assembly, chirality inversion or reconstruction under external stimuli, and kinetic regulation under non-equilibrium conditions47–49. This multilevel chirality evolution lays a structural foundation for the development of stimuli-responsive chiral materials, chiral devices, and asymmetric catalytic platforms50–53. Furthermore, supramolecular chirality mediated by covalent or topochemical reactions offers a promising framework for the dynamic construction of advanced functional systems with chiral responsiveness25,54–56.

In this work, we introduce disulfide bond cleavage and aromatic nucleophilic substitution (SNAr) reaction57,58. A pyrene-conjugated cystine derivative self-assembles into helical structures, which encounters a reductant TCEP undergoing disulfide bond cleavage into cysteine (Fig. 1). In situ reaction (SS to SH) is quantitative in the self-assembled state, arising evolution of molecular arrangement. The supramolecular chirality is inherited from the pristine templates and distinct from the as-synthesized SH. Such reaction-mediated sacrificial templating protocol represents a top-down process in contrast to that of bottom-up. Further verification of such effect was carried out in a complex two-component system. Introducing pentafluoropyridine (PFP) provides significant π-hole/π interactions to give coassemblies (SS/PFP), which undergo reduction into another form (SH/PFP). Interestingly, under gentle heating with weak base (NaHCO3), SNAr occurs to give SPFP. The conversion yield from SS/PFP to SPFP in the aggregate state is determined up to 67%, which leads to the profound changes in the self-assembly behaviors and chiroptical activities. In the multiple step process, the evolution of chirality also exhibits inheritance or templating effect. Furthermore, the current protocol complements non-covalent chemistry by facilitating the construction of chiroptical materials and nanoarchitectures that are otherwise challenging to achieve.

Results
Disulfide bond is dynamic and redox sensitive. Its cleavage can be readily realized by reductant. SS with a cystine skeleton in the presence of a reductant TCEP transforms into SH (Fig. 2a, Supplementary Figs. 1-11). In dimethyl sulfoxide (DMSO), the disulfide bond cleavage was monitored by 1H nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS), which verified near quantitative conversion at ambient conditions (Fig. 2b). Fourier transform infrared (FTIR) spectroscopy confirms the emergence of S-H stretching vibration bands after reaction (Fig. 2c and Supplementary Fig. 12). The reaction leads to conformational variations. In DMSO with a high polarity, an excimer band at around 490 nm is retained (Fig. 2d), illustrating the π-π stacking between pyrenes that SS adopts a folded geometry. Introducing TCEP witnesses the gradual disappearence of excimer emission, causing a luminescence color evolution from cyan to blue. The disulfide bond cleavage is dynamic and reversible59,60. Spontaneously, incubation at ambient conditions shall recover the cyan luminescence, and the redox process is reversible for several cycles (Fig. 2e). We also evaluated the circular dichroism (CD) response (Fig. 2f and Supplementary Figs. 13, 14). SS possesses a bisignate Cotton effect centered at around 350 nm caused by the folded pyrenes, while SH affords an intrinsic Cotton effect with decreased intensity due to the absence of aromatic interplay in solution. Then, we explored the disulfide cleavage interaction conducted in the self-assembled state (in bulk water with less DMSO). During the initial self-assembly process, the assembly of SH and SS undergoes liquid–liquid phase separation (LLPS), which serves as a critical intermediate stage before the eventual formation of stable nanostructures, as directly visualized by SEM and TEM (Supplementary Figs. 15–26, 28–39). This LLPS transition profoundly influences the chiral evolution of the assemblies. In particular, our in situ chiroptical measurements (CD and UV–Vis spectra, Supplementary Figs. 27 and 40) revealed that the CD signals, especially the Cotton effect around 350 nm, underwent dramatic changes, including complete inversion, during the LLPS process before eventually stabilizing. Within the confined and dynamic environment of the LLPS droplets, molecular packing modes, interaction barriers, and nucleation pathways are altered. This allows the emergence of chiral conformations that can compete with or even override the initial chiral information. The eventual CD equilibrium corresponds to the thermodynamically or kinetically favored chirality after this complex maturation and selection process mediated by LLPS. Thus, the evolution of CD signals through the LLPS stage provides direct spectroscopic evidence that phase separation dynamically perturbs, and can ultimately redefine, the chiral outcome of the assembly61. Hydrophobic force drives the aggregation of SS, which encounters TCEP shall rapidly transform into SH in an in situ manner. The reaction in the self-assembled state is still efficient and can be completed within 15 mins (more TCEP is however required). High-performance liquid chromatography (HPLC) analysis on the collected self-assemblies treated by TCEP indicates a near quantitative conversion efficiency (Fig. 2g). This reaction could overcome the barrier of aggregates and achieve the in-situ transformation, favoring the topochemical process. It also realizes a profound blue-shift emission from 500 nm to 400 nm (Fig. 2h). SH no doubt adopts a distinct aromatic stacking that disfavors the excimer emission (such as CH-π), whereby the reaction degree could be well illustrated by the maxima emission wavelength. Individual SS and SH (as-synthesized) in the assembled state exhibit distinct Cotton effect (Fig. 2i). The dichroism intensity is enhanced compared to the monomer state in Fig. 1f, and both SS and SH give rise to overall bisignate type signal due to interplay between hydrophobic pyrenes. When conducted by in-situ protocol, SH in-situ display totally different shaped CD signal with SH or SS (Fig. 2j). It implies the topochemical transformation could retain the chiral properties of pristine structures with specific variations. We also evaluated the CPL properties of SS, SH and SH in-situ in the self-assembled state (Fig. 2k, l and Supplementary Fig. 41). Remarkably, SS and SH give opposite-handed CPL signal ascribed to the different stacking of pyrenes. However, the SH in-situ samples transformed directly from SS aggregates display same handedness with SS. It reflects a strong chiral inheritance effect. Topochemical conversion is not a bottom-up self-assembly process, but can be classified as a top-down process with a sacrificial templating feature. Based on the pathway-dependent chiroptical properties of SH assembly, we developed a fluorescence-based encryption strategy. Initially, the SS assembly exhibits green fluorescence originating from pyrene excimers, while the SH assembly emits blue monomer fluorescence, which allows the pre-encrypted message to be read visually. Encryption is initiated by adding TCEP to the SS assembly, which cleaves the disulfide bonds and shifts the fluorescence from green to blue, thereby erasing the original information. Although the encrypted SS assembly (after TCEP treatment) and the original SH assembly both show similar blue fluorescence under UV light, they possess distinct chiroptical signals due to their different assembly pathways. Decryption is accomplished through chiroptical spectroscopy (CD or CPL), where the unique Cotton effects associated with each assembly pathway allow the hidden pattern to be recovered. Under visible light, all samples appear identical, providing an additional layer of security. This pathway-encoded strategy prevents decryption based solely on the final chemical state, demonstrating considerable potential for anti-counterfeiting applications. The SS pristine aggregate provides a chiral template or environment to refine the Cotton effect, CPL and other properties like nanomorphology.

Next, we explored the evolution of nanoarchitectures and their molecular packing using scanning electron microscopy (SEM) and grazing incidence wide angle X-ray scattering (GIWAXS). SS individually self-assembled into fibrous structures (Fig. 3a and Supplementary Figs. 43–46), most of which adopt a twisted topology. LSS and DSS respectively give homochiral right-handedness (P) and left-handedness (M). It implies the high-fidelity chirality transfer from molecular to macroscopic scale. The expression of chirality at macroscopic level is facilitated by the one-dimensional packing, and folded pyrene with relatively rigid skeleton favors the packing into helical sense. In comparison, SH (pre-synthesized) tends to crystallize into microrods. The three-dimensional growth hinders the chiral expression at macroscopic scale. The missing of disulfide bond leads to the unfolding without intramolecular constraints that improves the ordered packing. In contrast, we synthesized the self-assemblies from SH in-situ by directly adding TCEP to the SS aggregates. In the similar way, it observed the emergence of microrods with highly crystalline domains. However, the architectures are relatively larger than that of SH alone, which might be originated from the slow molecular exchange between reagents and products with more thermodynamic control pathways. It should be noted, even those SH and SH in-situ did not show macroscopic chirality probed by SEM, their chiroptical responses verified the presence of supramolecular chirality, which are accounted to the local or overall asymmetric packing of building units. Given the significant (approximately 200-fold) increase in particle width upon reduction, it is likely that the assemblies underwent partial or complete structural reorganization into a new form in the SH state. Nevertheless, the distinct chiroptical spectral differences strongly suggest that the original SS assemblies acted as seeds or templates during reduction, thereby guiding the asymmetric stacking orientation of the newly formed SH assemblies. This observation demonstrates an effective chiral transfer or chiral memory effect. GIWAXS provides detailed and anisotropic molecular packing information, where Qxy and Qz record the lattice parameters perpendicular and parallel to the one-dimensional growth direction (inset of Fig. 3b). Based on the 2D scattering pattern and the corresponding integral profiles, Qz and Qxy bands are basically locate below and higher than 1.0 Å−1. For SS, the several pronounced peaks at Qz direction are assigned as the lattice parameters, and the primary d-spacing of 13.4 Å can be designated as the interlayer distance (molecular length of a SS). 3.8 and 3.17 Å correspond to the π-π stacking of pyrenes. SH apparently adopts a distinct packing modality. The 1st and 2nd d-spacings at 8.72 and 6.54 Å show that it is in an interdigitated array with shrunk packing parameters. The Qxy plane with three major bands of 3.56, 3.23 and 2.90 Å is contributed by the π-π and CH-π short contacts between pyrenes. SH in-situ has scattering patterns different with both SH and SS. There are larger d-spacings found at Qz direction including 12.3 and 10.3 Å, confirming the templating effects of SS. A sharp band at 3.47 Å is accounted to the packing of pyrenes. The results are in good agreement with the chiral inheritance found in CD and CPL activities.

The above discussions illustrate the disulfide bond cleavage into SH with great changes in nanoarchitectures with chiral inheritance. Due to the presence of folded pyrene moieties, SS might be capable of clamping or coassemble with electron-deficient compounds through π-hole/π interactions62,63. Thereafter, we could realize disulfide bond cleavage in a two-component system (Fig. 4a). PFP with a perfluorinated aromatic core was introduced. In self-assembled state, the gradual addition of excess PFP witnesses the enhanced monomeric emission of SS (Fig. 4b, excess PFP was added in order to overcome its solvation effect). It implies that PFP inserts into the aromatic packing arrays to afford coassembled arrangements. Decreasing tendency was found in CD spectra upon adding PFP (Fig. 4c and Supplementary Fig. 47). Between 325 nm to 400 nm, the pristine intrinsic Cotton effects becomes bisignate ascribed to the aromatic complexation between pyrenes and PFPs. SEM images on the two-component coassemblies show the similar twisted fibers with identical handedness that LSS/PFP and DSS/PFP give rise to P- and M-handedness (Fig. 4d and Supplementary Figs. 48, 49). We did not observe the presence of phase separation or self-sorting of individual aggregation. It is believed that partial insertion of PFP into the coassembly array of SS which act as a chiral matrix is plausibly a dominating pathway. Using different equiv. of TCEP to control the cleavage degree of disulfide bond, SS/PFP gradually converted to SH/PFP, with decreasing excimer emission and enhanced monomeric emission at around 400 nm (Fig. 4e). The normalized emission spectra display difference with the SS sample without PFP (Fig. 2h). SS/PFP exhibits strong and persistent band at around 400 nm because PFP could bind to pyrenes either in the SS or SH form. CD spectra, however, were hardly altered after disulfide bond cleavage. It further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP.

SH/PFP coassembly system is potentially reactive. The para-position F could readily be substituted by sulfhydryl group catalyzed by base. After optimization, the reaction could be initiated in solution (DMSO) in the presence of gentle heating and a weak base NaHCO3 (Fig. 5a). The product of SPFP was obtained and fully characterized by 1H, 19F NMR and HRMS (Fig. 5b). It allows for an alternative protocol to enable topochemical conversion. However, it still faces one big challenge that how efficient the SNAr can be in the self-assembled state. A two-step in situ conversion was conducted. SS/PFP coassemblies were prepared, followed by the addition of TCEP. After incubation, NaHCO3 powder was then added. The final mixture was incubated in a 60°C oven. Then the self-assemblies were collected by high-speed centrifuge, and subjected to HPLC analysis (Fig. 5c). It shows that the presence of SPFP after two in-situ steps, which gives a 67% yield. There is almost no side product with however remaining SH. It illustrates the pathway is feasible to give topochemically self-assembled products. One pronounced behavior is the changes of fluorescence. S-substituted PFP constitutes into a typical D-π-A conjugate with cyan emission. Therefore, the addition of NaHCO3 to SH/PFP system enables the luminescent color evolution from blue to cyan (~490 nm, Fig. 5d). The CD spectra show different features with the SH/PFP (Fig. 5e and Supplementary Fig. 55), that strong exciton bands were observed between 400 to 250 nm, implying the electronic interplay between the aromatic planes. This reaction promotes us to further explore the templating effect between as-synthesized and in-situ converted SPFP. Probed by CPL (Fig. 5f and Supplementary Fig. 56), the two-step in-situ sample show stronger CPL intensity as well as the dissymmetry g-factors (±0.005) than the as-synthesized SPFP (±0.002). It is plausibly stemmed from the chiral inheritance effect as SS has a preference self-assembling into helical structures with enhanced chiral expression. It is worth noting that, the CPL of in-situ converted SPFP is blue-shifted compared to that of as-synthesized samples, which is caused by the incomplete conversion as discussed in Fig. 4c. With respect to nanomorphology, SPFP alone affords an achiral long and thin fibers (Fig. 5g and Supplementary Figs. 57–59). SPFP alone failed to express chirality at macroscopic scale. The nanoarchitectures were greatly altered undergoing a topochemical process. Starting from SH/PFP, the SPFP in-situ gives ribbon-like geometry with enlarged size to micro-scale, which stems from the giant crystalline states of SH coassembly. In contrast, SPFP in-situ underwent two-step topochemical process starting from SS/PFP is chiral. It illustrates the vital importance of templating and inheritance effect of starting materials, which also in consistent with the strong CPL g-factor compared to the as-synthesized SPFP.

Finally, we carried out molecular dynamics (MD) simulation to gain a deep understanding about the aggregation in different combinations (Supplementary Figs. 60–64). Five self-assembly systems including SS, SH, SS/PFP, SH/PFP and SPFP were conducted under same simulation conditions. The free monomers have propensity to form aggregates accompanied by the desolvation. Solvophobic force, hydrogen bonding and aromatic stacking are recognized as the major contributions to aggregation. We analyzed the dominant dimer structures extracted from LSS MD simulations. By fixing the pyrene rings and optimizing the amino acid residues, the LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole/π forces. In-situ fabrication of SH/PFP coassembly produced relatively larger constructs. This behavior is quite similar to the system without PFP. The LSH and LSPFP further confirms the presence of templating and chiral inheritance effect during the topochemical process (Fig. 4f and Supplementary Fig. 50). SS/PFP and SH/PFP are both CPL active (Fig. 4g, h and Supplementary Fig. 51), and both exhibit l- and r-CPL in the D- and L-enantiomeric form with however different maxima wavelengths at 500 and 400 nm respectively. The in-situ generated coassemblies of SH/PFP in-situ show similar feature to SH/PFP due to the complete conversion from SS to SH in the aggregated state. SEM probed the morphologies of PFP coassemblies (Fig. 4i and Supplementary Figs. 52–54). Incorporating PFP into SH (as-synthesized) assembly witnesses the presence of nanorods with lateral width and length rather smaller than SH alone. Clearly, coassembly with a second component decreases the three-dimensional tendency by directional π-hole

Methods

Peer review rounds
[{"round": 1, "reviewer_comments": {"reviewer_1": "In this work Wang et al. report on the assembly and transformation via reduction of a disulfide bond in an assembled aggregated. Across these transformations via chemical reduction the chiral nature of the assembly purportedly informs the resulting chirality of the produced ensemble containing the reduced thiol moieties, which differs from the assembly chirality of the directly self-assembled thiol system. SEM and GIWAXS were used to investigate the structure of the assemblies. SEM revealed helical fibers for the disulfide and significantly larger rods for the thiol (2 orders of magnitude change in width), both from direct assembly and in situ reduction of the disulfide assembly. GIWAXS experiments revealed appreciable differences between the directly assembled disulfide and thiol, with the in situ produced thiol being appreciably less ordered. The disulfide was the then mixed with a fluorinated arene towards mixed assembly of pi-rich and pi-poor arenes. It was demonstrated that upon reduction and deprotonation, the resulting thiolate moieties performed nucleophilic aromatic substitution of the fluorinated pyridine, where the initial chirality of the disulfide assembly appears to influence the presence of chirality of the final product. Finally, MD simulations were performed to examine the assembly of the disulfide with the fluorinated arene, leading to the observation of pi-based stacking interactions.\nIt is the opinion of this reviewer that this work is not suitable for publication in Nature Communications.\nThere is no appreciable conceptual advanced provided, with the crux of the work being reduction of disulfides and nucleophilic aromatic substitutions occurring in a solvated assembly (that most likely is in appreciable equilibrium with full solvation). Both reactions have been studied extremely extensively across innumerable platforms, from small molecules to biological assemblies, namely peptides and proteins.\nGiven the immense differences in the size of the assemblies between the disulfide state and reduced state (200 times wider particles upon reduction), it appears to very likely that upon reduction the system is fully re-organizing into new assemblies.\nMany of the explanations put forth in the manuscript as to the observed phenomenon are conjecture and are not experimentally supported through the requisite spectroscopic characterization of (inter)molecular interactions.\nEffectively relying on macroscopic measurements of chirality to make conclusions about molecular interactions is unreliable at best.\nIn total, this work does not present an appreciably novel concept, nor is it scientifically rigorous.", "reviewer_2": "In this manuscript, the authors reported the coassembly of aromatic cystine derivative with PFP, and represented strong templating and chiral inheritance effect through multiple topochemical steps. Several technologies including NMR, HR-MS, UV, CD, FTIR, Fluorescence, CPL, SEM and GIXS have been adopted to characterize the samples and the critical topochemical conversion has been proven strongly by the well-designed experiments. The results are generally convincing. The images were nice-showing. All these data did show a well-defined chiral inheritance effect when all the enantiomers pairs are compared.\n\" And the current protocol facilitates the construction of chiroptical materials and nanoarchitectures that noncovalent chemistry could not accomplish. \" This sentence is suggested being reconsidered and balanced. Noncovalent chemistry plays a leading role in this work, although the disulfide bond was employed.\nIt's interesting to observe the helical inheritance of the resulting nanostructures. Do the oligmers or nuclei formed at the initial stage influence the chirality? If liquid-liquid phase separation occured, can the chiral inheritance be disturbed?\nIs it possible that the MD simulation can provide clues for structural chiral of the self-assembly of SS? Is it possible to give the fundamental molecular arrangement of the topochemical conversion (For example, the difference between SS and SH) using MD or DFT?\nThe potential application and faced limitations are suggested discussion on the present chiral nanostructures in comparison to the reported one.\nThe relevant exmples regarding the chiral self-assembly (Colloids Surf A 2015, 469, 263-270; Matter 2023, 6, 1945-1963; J Am Chem Soc 2024, 146,18104-18116) are suggested reference and discussion based on the context of this work.", "reviewer_3": "The manuscript presents a novel study on chiral inheritance phenomena in cystine-based coassemblies undergoing topochemical transformations, including disulfide bond cleavage and nucleophilic aromatic substitution. This work addresses an important topic at the interface of supramolecular chemistry, dynamic covalent chemistry, and chiroptical materials. The experimental design is comprehensive, integrating spectroscopy, microscopy, GIWAXS, and molecular dynamics simulations. The findings provide valuable insights into templating and inheritance effects in confined self-assembled states. The manuscript is well written and overall of high scientific quality. I recommend minor revision prior to acceptance.\nComments:\n1.The authors suggest potential applications in chiroptical materials; however, no prototype demonstration is provided. Including even a preliminary proof-of-concept device would substantially enhance the impact and broaden the readership appeal.\n2.Several typographical errors should be corrected, such as “luminescencec” (p.11) and the repeated use of “conversed” instead of “converted.”\n3.In Figure 1d, the label “DCEP” appears to be a typographical mistake and should be corrected to “TCEP.”"}, "author_response": "Response letter\nReviewer #1: ... [Authors' response text omitted for brevity in this example, but would be included here in full] ... Reviewer #2: ... [Authors' response text] ... Reviewer #3: ... [Authors' response text]"}, {"round": 2, "reviewer_comments": {"reviewer_1": "No changes have been made to the manuscript to alter this reviewer's previous interpretation of and opinion of manuscript.", "reviewer_3": "I have carefully reviewed the revised manuscript and the authors' point-by-point responses. I am satisfied with the revisions made, which have addressed all of my previous concerns adequately. The manuscript is now significantly improved in clarity and scientific rigor.I have also look over the responses of the authors to the concerns from Reviewer #2. The authors have properly addressed the technical concerns raised by reviewer #2. I recommend acceptance of the manuscript in its current form."}, "author_response": ""}]

Decision letter