DOI: 10.5061/dryad.tqjq2bw8z
title: Synthesis of photoresponsive liquid crystal elastomers: A general chemical approach

description: Liquid crystal elastomers represent a versatile class of polymer materials
 with potential applications in soft robotics, adhesives, and smart
 materials. The integration of photoresponsive molecules into LCEs enables
 spatiotemporal control, wavelength-selective actuation and remote
 operations, expanding their application space. However, the incorporation
 of sensitive photoresponsive molecules is often hindered by the chemical
 methods and processing conditions required for the LCE fabrication. In
 this work, we introduce a general strategy for covalent incorporation of
 photoresponsive moieties into LCEs through Diels–Alder chemistry,
 utilizing late-stage functionalization. This approach facilitates the
 retention of material alignment and thermomechanical properties, while
 enabling the functionalization of thick, aligned polysiloxane elastomers.
 A wide range of photoresponsive molecules, including azobenzenes,
 spiropyrans, cyanine dyes, and donor-acceptor Stenhouse adducts, were
 successfully integrated, demonstrating this method’s versatility.
 Furthermore, we leverage the reversible nature of Diels–Alder conjugation
 to achieve on-demand editing and exchange of photoresponsive moieties
 within a single LCE, allowing for dynamic tuning of material properties.
 This platform offers a scalable and efficient route for developing
 multifunctional LCEs, providing new opportunities for advanced
 stimuli-responsive materials and broadening the scope of applications
 across various fields.
description: # Synthesis of photoresponsive liquid crystal elastomers: A general
 chemical approach
 [https://doi.org/10.5061/dryad.tqjq2bw8z](https://doi.org/10.5061/dryad.tqjq2bw8z) ## Description of the data and file structure Data from peer-reviewed article: Title: Synthesis of Photoresponsive Liquid Crystal Elastomers: A General Chemical Approach Authors: Jesus Guillen Campos, Minwook Park, Yuhang Wu, Sara Sandlass, Egor Novikov, Sophia Bailey, Michael Gordon, Tatiana Timofeeva and Javier Read de Alaniz Corresponding author: Javier Read de Alaniz, [javier@chem.ucsb.edu](mailto:javier@chem.ucsb.edu) \----------------------------------------------------------------------------------------------------------------- ### Files and variables #### File: Text\_files.zip File List 1\)Figure 2B 2\)Figure 2C 3\)Figure 4A 4\)Figure 4B 5\)Figure 4C 6\)Figure 4D 7\)Figure 6C 8\)Figure 6D 9\)Figure S1 10\)Figure S4 11\)Figure S5 12\)Figure S7 13\)Figure S8 14\)Figure S9 15\)Figure S10 16\)Figure S11 17\)Figure S12 18\)Figure S13 19\)Figure S14 20\)Figure S15 21\)Figure S16 22\)Figure S17 23\)Figure S18 24\)Figure S19 25\)Figure S20 26\)Figure S21 27\)Figure S22 28\)Figure S23 29\)Figure S24 30\)Figure S25 31\)Figure S26 32\)Figure S32 33\)Figure S33 34\)Figure S34 35\)Figure S35 36\)Figure S36 37\)Figure S37 38\)Figure S38 39\)Figure S39 40\)Figure S40 41\)Figure S41 42\)Figure S42 43\)Figure S43 44\)Figure S44 45\)Figure S45 46\)Figure S46 47\)Figure S47 48\)Figure S48 49\)Figure S49 50\)Figure S50 51\)Figure S51 52\)Figure S72 53\)Figure S73 54\)Figure S74 55\)Figure S75 56\)Figure S76 57\)Figure S77 58\)Figure S78 59\)Figure S79 60\)Figure S80 61\)Figure S81 62\)Figure S82 63\)Figure S83 64\)Figure S84 65\)Figure S102 66\)Figure S103 67\)Figure S104 68\)Figure S105 69\)Figure S106 70\)Figure S107 71\)Figure S108 72\)Figure S109 73\)Figure S110 74\)Figure S111 \----------------------------------------------------------------------------------------------------------------------- 1\)Figure 2B 1H NMR traces of the hydrosilylation reaction of the furan handle with PHMS from 0 to 60 minutes where consumption of the terminal vinyl group is monitored while the integration of furan aromatic hydrogens remains constant. ``` row 1: Chemical shift (ppm) row 2: Spectrum after 0 min (a. u.) row 3: Spectrum after 5 min (a. u.) row 4: Spectrum after 30 min (a. u.) row 5: Spectrum after 60 min (a. u.) ``` The previous results were extracted from the integrations using the Mestrenova integration function over the indicated area in the manuscript and the total set of raw HNMR data can be found in the corresponding data attached to figure S1. \----------------------------------------------------------------------------------------------------------------------- 2\)Figure 2C Plot of the conversion of the hydrosilylation reaction. ``` row 1: Time (min) row 2: Furan1 (% conversion) row 3: Vinilgemhidrogen (% conversion) row 4: formation (% conversion) ``` \----------------------------------------------------------------------------------------------------------------------- 3\)Figure 4A Plot of the effect of the PRM loading in the LCE in the glass transition temperature as recorded by DSC at a heating rate of 10 °C per minute. ``` row 1: Furan loading (wt. %) row 2: Glass transition temperature Furan LCE (Degree Celsius) row 3: Glass transition temperature Red dye (Degree Celsius) row 4: Glass transition temperature Azobenzene (Degree Celsius) row 5: Glass transition temperature Spiropyran (Degree Celsius) row 6: Glass transition temperature DASA (Degree Celsius) row 7: Glass transition temperature Blue dye (Degree Celsius) ``` The previous results were extracted from the mid-point of the second order phase transition seen in the calorigram between -20 and 20 degrees Celsius. Such raw data corresponding to the full temperature scan can be found in the file of Figure S4, Figure s24, Figure S25 and Figure S26 \----------------------------------------------------------------------------------------------------------------------- 4\)Figure 4B Effect of the loading of the PRM in the nematic to isotropic temperature obtained by DSC. ``` row 1: Furan loading (wt. %) row 2: Nematic to isotropic temperature Furan LCE (Degree Celsius) row 3: Nematic to isotropic temperature Red dye (Degree Celsius) row 4: Nematic to isotropic temperature Azobenzene (Degree Celsius) row 5: Nematic to isotropic temperature Spiropyran (Degree Celsius) row 6: Nematic to isotropic temperature DASA (Degree Celsius) row 7: Nematic to isotropic temperature Blue dye (Degree Celsius) ``` The previous results were extracted from the local minima of the pseudo first order phase transition seen in the calorigram between 20 and 100 degrees Celsius. Such raw data corresponding to the full temperature scan can be found in the file of Figure S4, Figure s24, Figure S25 and Figure S26 \----------------------------------------------------------------------------------------------------------------------- 5\)Figure 4C Order parameter as a function of the introduced PRM determined by 2D WAXD. ``` row 1: Furan loading (wt. %) row 2: Order parameter Furan LCE (unitless) row 3: Order parameter Red dye (unitless) row 4: Order parameter Azobenzene (unitless) row 5: Order parameter Spiropyran (unitless) row 6: Order parameter DASA (unitless) row 7: Order parameter Blue dye (unitless) ``` The previous results were extracted from the half-with of the plots of intensity as a function of the azimuthal angle using the equation S(order parameter)=|(half width-180)/180|. Such raw data corresponding to the full azimuthal angle scan can be found in the file of Figure S32 to Figure S51. \----------------------------------------------------------------------------------------------------------------------- 6\)Figure 4D Linear dichroism of the introduced PRMs in the siloxane LCEs determined by polarized UV-Vis spectroscopy. ``` row 1: photoresponsive molecule (na) row 2: parallel absorbance (a. u.) row 3: perpendicular absorbance (a. u.) row 4: dichroic value (unitless) ``` The previous results were extracted from the linear absorbance as a function of film tilt angle. Such data can be found in the files provided from Figure S75 to Figure S79. \----------------------------------------------------------------------------------------------------------------------- 7\)Figure 6C Solid-state absorbance trace of the disperse red dye LCE before editing. ``` row 1: Wavelength (nm) row 2: Absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 8\)Figure 6D Solid-state absorbance trace of the edited DASA LCE. ``` row 1: Wavelength (nm) row 2: Absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 9\)Figure S1 CDCl3 1H NMR trace of the reaction of linear PHMS with the furan handle in the presence of platinum catalyst at 70 °C in CDCl3toluene. ``` row 1: Chemical shift (ppm) row 2: Spectrum after 0 min (a. u.) row 3: Spectrum after 5 min (a. u.) row 4: Spectrum after 10 min (a. u.) row 5: Spectrum after 30 min (a. u.) row 6: Spectrum after 40 min (a. u.) row 7: Spectrum after 20 min (a. u.) row 8: Spectrum after 60 min (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 10\)Figure S4 Differential Scanning Calorimetry of furan functionalized LCEs at different furan loadings. ``` row 1: Temperature Finkelmann (Degree Celsius) row 2: Heat flow Finkelmann (W/g) row 3: Temperature Furan Handle 1 % (Degree Celsius) row 4: Heat flow Furan Handle 1 % (W/g) row 5: Temperature Furan Handle 5 % (Degree Celsius) row 6: Heat flow Furan Handle 5 % (W/g) row 7: Temperature Furan Handle 10 % (Degree Celsius) row 8: Heat flow Furan Handle 10 % (W/g) ``` \----------------------------------------------------------------------------------------------------------------------- 11\)Figure S5 Nematic to isotropic and glass transition temperatures as a function of the added furan handle. ``` row 1: Furan loading (wt. %) row 2: Glass transition temperature (Degree Celsius) row 3: Nematic to isotropic temperature (Degree Celsius) ``` \----------------------------------------------------------------------------------------------------------------------- 12\)Figure S7 Change in the order parameter as a function of added furan handle determined by 2D WAXD. ``` row 1: Furan loading (wt. %) row 2: Order parameter (unitless) ``` \----------------------------------------------------------------------------------------------------------------------- 13\)Figure S8 2D WAXD of the Finkelmann films before and after high vacuum for three days. ``` row 1: Azimuthal angle of the film before drying (Degrees) row 2: Intensity of the film before drying (a. u.) row 2: Azimuthal angle of the film after drying (Degrees) row 4: Intensity of the film before drying (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 14\)Figure S9 Normalized UV-Visible spectrum of DASA-maleimide in THF. ``` row 1: Wavelength (nm) row 2: Absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 15\)Figure S10 Normalized UV-Visible spectrum of blue dye-maleimide in THF. ``` row 1: Wavelength (nm) row 2: Absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 16\)Figure S11 Normalized UV-Visible spectrum of azobenzene-maleimide in THF. ``` row 1: Wavelength (nm) row 2: Absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 17\)Figure S12 Normalized UV-Visible spectrum of disperse red dye-maleimide in THF. ``` row 1: Wavelength (nm) row 2: Absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 18\)Figure S13 Normalized UV-Visible spectrum of spiropyran-maleimide in THF. ``` row 1: Wavelength (nm) row 2: Absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 19\)Figure S14 Spectroscopic calibration curve of DASA-maleimide at 640 nm in THF. ``` row 1: Concentration (M) row 2: Absorbance at 640 nm (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 20\)Figure S15 Spectroscopic calibration curve of blue dye-maleimide at 655 nm in THF. ``` row 1: Concentration (M) row 2: Absorbance at 655 nm (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 21\)Figure S16 Spectroscopic calibration curve of azobenzene-maleimide at 350 nm in THF. ``` row 1: Concentration (M) row 2: Absorbance at 350 nm (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 22\)Figure S17 Spectroscopic calibration curve of disperse red dye-maleimide at 475 nm in THF. ``` row 1: Concentration (M) row 2: Absorbance at 475 nm (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 23\)Figure S18 Spectroscopic calibration curve of spiropyran-maleimide at 340 nm in THF. ``` row 1: Concentration (M) row 2: Absorbance at 340 nm (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 24\)Figure S19 Absorbance of azobenzene-functionalized LCE (0.5 wt. %) in the solid state. ``` row 1: Wavelength (nm) row 2: absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 25\)Figure S20 Absorbance of disperse red dye-functionalized LCE (0.5 wt. %) in the solid state. ``` row 1: Wavelength (nm) row 2: absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 26\)Figure S21 Absorbance of spiropyran-functionalized LCE (0.5 wt. %) in the solid state. ``` row 1: Wavelength (nm) row 2: absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 27\)Figure S22 Absorbance of blue dye-functionalized LCE (0.5 wt. %) in the solid state. ``` row 1: Wavelength (nm) row 2: absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 28\)Figure S23 Absorbance of DASA-functionalized LCE (0.5 wt. %) in the solid state. ``` row 1: Wavelength (nm) row 2: absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 29\)Figure S24 Differential Scanning Calorimetry of photoswitch functionalized LCEs at 1 wt. % furan loading. ``` row 1: Temperature Azobenzene 1 wt % row 2: Heat flow Azobenzene 1 wt % row 3: Temperature Red dye 1 wt % row 4: Heat flow Red dye 1 wt % row 5: Temperature Spiropyran 1 wt % row 6: Heat flow Spiropyran 1 wt. % row 7: Temperature Blue dye 1 wt. % row 8: Heat flow Blue dye 1 wt. % row 9: Temperature DASA 1 wt. % row 10: Heat flow DASA 1 wt. % ``` \----------------------------------------------------------------------------------------------------------------------- 30\)Figure S25 Differential Scanning Calorimetry of photoswitch functionalized LCEs at 5 wt. % furan loading. ``` row 1: Temperature Azobenzene 5 wt % row 2: Heat flow Azobenzene 5 wt % row 3: Temperature Red dye 5 wt % row 4: Heat flow Red dye 5 wt % row 5: Temperature Spiropyran 5 wt % row 6: Heat flow Spiropyran 5 wt. % row 7: Temperature Blue dye 5 wt. % row 8: Heat flow Blue dye 5 wt. % row 9: Temperature DASA 5 wt. % row 10: Heat flow DASA 5 wt. % ``` \----------------------------------------------------------------------------------------------------------------------- 31\)Figure S26 Differential Scanning Calorimetry of photoswitch functionalized LCEs at 10 wt. % furan loading. ``` row 1: Temperature Azobenzene 10 wt % row 2: Heat flow Azobenzene 10 wt % row 3: Temperature Red dye 10 wt % row 4: Heat flow Red dye 10 wt % row 5: Temperature Spiropyran 10 wt % row 6: Heat flow Spiropyran 10 wt. % row 7: Temperature Blue dye 10 wt. % row 8: Heat flow Blue dye 10 wt. % row 9: Temperature DASA 10 wt. % row 10: Heat flow DASA 10 wt. % ``` \----------------------------------------------------------------------------------------------------------------------- 32\)Figure S32 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of 0.5 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 33\)Figure S33 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of 5 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 34\)Figure S34 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of 10 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 35\)Figure S35 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of the original Finkelmann LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 36\)Figure S36 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of 1 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 37\)Figure S37 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of spiropyran-maleimide functionalized at 1 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 38\)Figure S38 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of blue dye-maleimide functionalized at 1 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 39\)Figure S39 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of disperse red dye-maleimide functionalized at 1 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 40\)Figure S40 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of azobenzene-maleimide functionalized at 1 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 41\)Figure S41 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of DASA-maleimide functionalized at 1 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 42\)Figure S42 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of DASA-maleimide functionalized at 5 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 43\)Figure S43 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of blue dye-maleimide functionalized at 5 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 44\)Figure S44 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of azobenzene-maleimide functionalized at 5 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 45\)Figure S45 . Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of spiropyarn-maleimide functionalized at 5 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 46\)Figure S46 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of Disperse red 1-maleimide functionalized at 5 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 47\)Figure S47 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of blue dye-maleimide functionalized at 10 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 48\)Figure S48 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of DASA-maleimide functionalized at 10 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 49\)Figure S49 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of spiropyran-maleimide functionalized at 10 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 50\)Figure S50 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of disperse red dye-maleimide functionalized at 10 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 51\)Figure S51 Intensity as a function of the azimuthal angle of the wide-angle X-ray scattering of azobenzene-maleimide functionalized at 10 wt. % furan in the LCE. row 1: Azimuthal angle (degrees) row 2: Intensity (a. u.) \----------------------------------------------------------------------------------------------------------------------- 52\)Figure S72 Glass transition temperature as a function of approximate loading of photoswitch. ``` row 1: Red dye loading row 2: Glass transition temperature row 3: Azobenzene loading row 4: Glass transition temperature row 5: Spiropyran loading row 6: Glass transition temperature row 7: Blue dye loading row 8: Glass transition temperature row 9: DASA loading row 10: Glass transition temperature ``` \----------------------------------------------------------------------------------------------------------------------- 53\)Figure S73 Nematic to isotropic temperature as a function of approximate loading of photoswitch. ``` row 1: Red dye loading row 2: Nematic to isotropic temperature row 3: Azobenzene loading row 4: Nematic to isotropic temperature row 5: Spiropyran loading row 6: Nematic to isotropic temperature row 7: Blue dye loading row 8: Nematic to isotropic temperature row 9: DASA loading row 10: Nematic to isotropic temperature ``` \----------------------------------------------------------------------------------------------------------------------- 54\)Figure S74 Order parameter as a function of approximate loading of photoswitch. ``` row 1: Red dye loading row 2: Order parameter row 3: Azobenzene loading row 4: Order parameter row 5: Spiropyran loading row 6: Order parameter row 7: Blue dye loading row 8: Order parameter row 9: DASA loading row 10: Order parameter ``` \----------------------------------------------------------------------------------------------------------------------- 55\)Figure S75 Polarized absorbance as a function of the angle of polarization of the disperse red dye-LCE at 0.5 wt. % loading of furan handle at wavelength of 488 nm with a 10 nm band was used at an intensity of 40.8 mW cm-2. ``` row 1: Angle (degrees) row 2: Polarized absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 56\)Figure S76 Polarized absorbance as a function of the angle of polarization of the azobenzene-LCE at 0.5 wt. % loading of furan handle. A 365 nm UV LED was used at an intensity of 26 mW cm-2. ``` row 1: Angle (degrees) row 2: Polarized absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 57\)Figure S77 Polarized absorbance as a function of the angle of polarization of the spiropyran-LCE at 0.5 wt.% loading of furan handle. This sample was characterized at a wavelength of 365 nm using a UV LED at 26 mW cm-2. ``` row 1: Angle (degrees) row 2: Polarized absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 58\)Figure S78 Polarized absorbance as a function of the angle of polarization of the blue dye-LCE at 0.5 wt.% loading of furan handle at 633 nm using an intensity of 95. 5 mW cm-2. ``` row 1: Angle (degrees) row 2: Polarized absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 59\)Figure S79 Polarized absorbance as a function of the angle of polarization of the DASA-LCE at 0.5 wt.% loading of furan handle at 633 nm using an intensity of 95. 5 mW cm-2. ``` row 1: Angle (degrees) row 2: Polarized absorbance (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 60\)Figure S80 Temperature as a function of time and light irradiation (purple highlight = 365 nm light, blue highlight = 430 nm light) for azobenzene-LCE at 1 wt.% loading of furan handle. ``` row 1: Time (s) row 2: Temperature (degree Celsius) ``` \----------------------------------------------------------------------------------------------------------------------- 61\)Figure S81 Temperature as a function of time and light irradiation (blue highlight = 430 nm light, yellow highlight = white light) for disperse red dye-LCE at 1 wt.% loading of furan handle. ``` row 1: Time (s) row 2: Temperature (degree Celsius) ``` \----------------------------------------------------------------------------------------------------------------------- 62\)Figure S82 Temperature as a function of time and light irradiation (red highlight = 660 nm light) for blue dye-LCE at 1 wt. % loading of furan handle. ``` row 1: Time (s) row 2: Temperature (degree Celsius) ``` \----------------------------------------------------------------------------------------------------------------------- 63\)Figure S83 Temperature as a function of time and light irradiation (red highlight = 660 nm light) for DASA-LCE at 1 wt. % loading of furan handle. ``` row 1: Time (s) row 2: Temperature (degree Celsius) ``` \----------------------------------------------------------------------------------------------------------------------- 64\)Figure S84 Temperature as a function of time and light irradiation (purple highlight = 360 nm light, yellow highlight = white light) for disperse red dye-LCE at 1 wt. % loading of furan handle. ``` row 1: Time (s) row 2: Temperature (degree Celsius) ``` \----------------------------------------------------------------------------------------------------------------------- 65\)Figure S102 1H NMR (500 MHz, CDCl3) spectra of disperse red dye-maleimide. ``` row 1: Chemical shift (ppm) row 2: Intensity (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 66\)Figure S103 13C NMR (125 MHz, CDCl3) spectra of disperse red dye-maleimide. ``` row 1: Chemical shift (ppm) row 2: Intensity (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 67\)Figure S104 1H NMR (500 MHz, CDCl3) spectra of furan handle. ``` row 1: Chemical shift (ppm) row 2: Intensity (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 68\)Figure S105 13C NMR (125 MHz, CDCl3) spectra of furan handle. ``` row 1: Chemical shift (ppm) row 2: Intensity (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 69\)Figure S106 1H NMR (500 MHz, CDCl3) spectra of Azobenzene-maleimide. ``` row 1: Chemical shift (ppm) row 2: Intensity (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 70\)Figure S107 13C NMR (125 MHz, CDCl3) spectra of azobenzene-maleimide. ``` row 1: Chemical shift (ppm) row 2: Intensity (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 71\)Figure S108 1H NMR (500 MHz, DMSO-d6) spectra of blue dye-maleimide. ``` row 1: Chemical shift (ppm) row 2: Intensity (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 72\)Figure S109 13C NMR (125 MHz, CDCl3) spectra of blue dye-maleimide. ``` row 1: Chemical shift (ppm) row 2: Intensity (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 73\)Figure S110 1H NMR (500 MHz, CDCl3) spectra of spiropyran-maleimide. ``` row 1: Chemical shift (ppm) row 2: Intensity (a. u.) ``` \----------------------------------------------------------------------------------------------------------------------- 74\)Figure S111 13C NMR (125 MHz, CDCl3) spectra of spiropyran-maleimide. ``` row 1: Chemical shift (ppm) row 2: Intensity (a. u.) ```