A Dual-Responsive Cationic Acridinium Nanohoop: Redox Activity and Acid/Base-Controlled Reversible Guest Capture and Release
Ming, Jiao; Zhang, Jin; Hu, Yan; Lan, Kai; Zhang, Dongmei; Li, Ping; Miao, Jiarong; Jiang, Jiyong; Zhang, Xiaobo; Zhong, Hanchi; Yu, Peiyuan; Cheng, Chuyang; Chemical Science  (2026) –; doi:10.1039/D6SC01132B

data_1577090
_publ_section_title
;
 A dual-responsive cationic acridinium nanohoop: redox activity and
 acid/base-controlled reversible guest capture and release.
;
_journal_issue                   21
_journal_name_full               'Chemical science'
_journal_page_first              10744
_journal_page_last               10754
_journal_paper_doi               10.1039/d6sc01132b
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety
'2(C67 H44 N), 2(C2 F3 O2), 4(C2 H F3 O2), 8(C7 H8), 2(C60)'
_chemical_formula_sum            'C322 H156 F18 N2 O12'
_chemical_formula_weight         4586.48
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-12-18
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-05-08 deposited with the CCDC.	2026-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                78.618(8)
_cell_angle_beta                 89.112(8)
_cell_angle_gamma                78.742(8)
_cell_formula_units_Z            1
_cell_length_a                   9.8726(18)
_cell_length_b                   17.269(3)
_cell_length_c                   31.681(5)
_cell_measurement_reflns_used    8702
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      42.288
_cell_measurement_theta_min      2.316
_cell_volume                     5191.7(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_av_unetI/netI     0.1505
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            41467
_diffrn_reflns_point_group_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        37.565
_diffrn_reflns_theta_max         37.565
_diffrn_reflns_theta_min         1.238
_exptl_absorpt_coefficient_mu    0.515
_exptl_absorpt_correction_T_max  0.7483
_exptl_absorpt_correction_T_min  0.6006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1726 before and 0.1050 after correction.
The Ratio of minimum to maximum transmission is 0.8026.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       needle
_exptl_crystal_F_000             2360
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Flack x determined using 2223 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.530
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     3215
_refine_ls_number_reflns         14490
_refine_ls_number_restraints     11258
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.2184
_refine_ls_R_factor_gt           0.1476
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3683
_refine_ls_wR_factor_ref         0.4298
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.777
_reflns_Friedel_fraction_max     0.777
_reflns_number_gt                8358
_reflns_number_total             14490
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6sc01132b2.cif
_cod_data_source_block           mj_2_0m
_cod_depositor_comments
'Adding full bibliography for 1577088--1577090.cif.'
_cod_database_code               1577090
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.861
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.80247
 0.19753
2. Restrained distances
 C320-C321
 1.51 with sigma of 0.02
 C47-C59 = C3-C2 = C7-C6 = C5-C4 = C15-C14 = C9-C10 = C8-C24 = C21-C40 = C31-
 C30 = C12-C11 = C43-C44 = C39-C38 = C53-C54 = C55-C56 = C29-C28 = C48-C49 =
 C58-C57 = C60-C46
 1.39 with sigma of 0.02
 C3-C15 = C2-C7 = C6-C22 = C5-C20 = C16-C15 = C14-C13 = C9-C8 = C21-C20 = C19-
 C18 = C36-C37 = C34-C33 = C31-C12 = C40-C39 = C52-C53 = C54-C55 = C28-C27 =
 C59-C58
 1.44 with sigma of 0.02
 C17-C18 = C16-C34 = C13-C1 = C23-C22 = C20-C19 = C36-C35 = C33-C32 = C26-C25 =
  C42-C41 = C37-C52 = C27-C45 = C50-C51
 1.38 with sigma of 0.02
 C1-C9 = C24-C25 = C23-C42 = C35-C54 = C11-C28 = C39-C50 = C52-C51 = C56-C30
 1.46 with sigma of 0.02
 C24-C23
 1.43 with sigma of 0.02
 C112-C111 = C112-C117 = C64-C65 = C63-C62 = C68-C69 = C67-C66 = C65-C77 = C77-
 C78 = C80-C84 = C81-C82 = C72-C73 = C75-C90 = C76-C88 = C87-C86 = C85-C104 =
 C84-C83 = C99-C98 = C98-C97 = C97-C119 = C96-C95 = C95-C94 = C93-C110 = C93-
 C92 = C90-C89 = C106-C114 = C103-C115 = C102-C101 = C101-C116 = C118-C117 =
 C118-C120 = C120-C111 = C110-C109 = C108-C113 = C115-C116
 1.45 with sigma of 0.02
 C112-C113 = C64-C63 = C68-C67 = C66-C65 = C79-C80 = C61-C98 = C69-C70 = C73-
 C92 = C83-C102 = C82-C99 = C95-C120 = C91-C90 = C106-C105 = C104-C103 = C101-
 C100 = C111-C110 = C114-C115 = C116-C117
 1.39 with sigma of 0.02
 C64-C79 = C63-C68 = C67-C72 = C66-C74 = C78-C79 = C80-C81 = C61-C69 = C73-C74
 = C75-C76 = C88-C89 = C86-C85 = C83-C82 = C92-C91 = C107-C106 = C105-C104 =
 C100-C119 = C113-C114
 1.44 with sigma of 0.02
 C77-C76 = C78-C86 = C81-C62 = C71-C72 = C74-C75 = C88-C87 = C85-C84 = C97-C96
 = C94-C93 = C89-C107 = C119-C118 = C109-C108
 1.38 with sigma of 0.02
 C62-C61 = C70-C96 = C71-C94 = C87-C105 = C99-C100 = C91-C109 = C107-C108 =
 C103-C102
 1.46 with sigma of 0.02
 C70-C71
 1.43 with sigma of 0.02
 C321-C322 = C321-C326 = C323-C324
 1.39 with sigma of 0.02
 C322-C323 = C324-C325 = C325-C326
 1.38 with sigma of 0.02
 C257-C258
 1.51 with sigma of 0.02
 C258-C259 = C258-C263 = C260-C261
 1.39 with sigma of 0.02
 C259-C260 = C261-C262 = C262-C263
 1.38 with sigma of 0.02
 C349-C351
 1.54 with sigma of 0.02
 C349-O348
 1.24 with sigma of 0.02
 C349-O350
 1.25 with sigma of 0.02
 C351-F352 = C351-F354 = C351-F353
 1.33 with sigma of 0.02
 C335-C337
 1.54 with sigma of 0.02
 C335-O334
 1.24 with sigma of 0.02
 C335-O336
 1.25 with sigma of 0.02
 C337-F338 = C337-F340 = C337-F339
 1.33 with sigma of 0.02
 C356-C358
 1.54 with sigma of 0.02
 C356-O355
 1.24 with sigma of 0.02
 C356-O357
 1.25 with sigma of 0.02
 C358-F359 = C358-F361 = C358-F360
 1.33 with sigma of 0.02
 C63-C61 = C68-C61 = C65-C78 = C77-C79 = C80-C83 = C81-C83 = C62-C69 = C70-C95
 = C70-C94 = C75-C89 = C75-C88 = C87-C104 = C99-C119 = C99-C97 = C96-C94 = C92-
 C109 = C107-C113 = C106-C113 = C103-C116 = C103-C101 = C102-C116 = C101-C115
 2.35 with sigma of 0.04
 C67-C71 = C78-C85 = C80-C62 = C70-C72 = C73-C91
 2.44 with sigma of 0.04
 C66-C73
 2.33 with sigma of 0.04
 C62-C98 = C82-C98 = C82-C100
 2.47 with sigma of 0.04
 C321-C323
 2.42 with sigma of 0.04
 C321-C325
 2.41 with sigma of 0.04
 C322-C324
 2.39 with sigma of 0.04
 C323-C325 = C324-C326
 2.4 with sigma of 0.04
 C257-C259 = C257-C263
 2.52 with sigma of 0.04
 C258-C260
 2.42 with sigma of 0.04
 C258-C262
 2.41 with sigma of 0.04
 C259-C261
 2.39 with sigma of 0.04
 C260-C262 = C261-C263
 2.4 with sigma of 0.04
 C349-F352 = C349-F354
 2.4 with sigma of 0.04
 C349-F353
 2.35 with sigma of 0.04
 C335-F338 = C335-F340
 2.4 with sigma of 0.04
 C335-F339
 2.35 with sigma of 0.04
 C356-F359 = C356-F361
 2.4 with sigma of 0.04
 C356-F360
 2.35 with sigma of 0.04
 C320-C326 \\sim C327-C329
 with sigma of 0.02
 C320-C326 \\sim C320-C322
 with sigma of 0.04
 C1-C13 \\sim C51-C50 \\sim C10-C9 \\sim C49-C48 \\sim C11-C12 \\sim C59-C47
\\sim C2-C3 \\sim C14-C15 ~
 C32-C33 \\sim C34-C16 \\sim C35-C36 \\sim C18-C17 \\sim C4-C5 \\sim C19-C20
\\sim C38-C39 \\sim C41-C42 ~
 C40-C21 \\sim C22-C23 \\sim C24-C8 \\sim C6-C7 \\sim C25-C26 \\sim C44-C43
\\sim C45-C27 \\sim C46-C60 ~
 C28-C29 \\sim C57-C58 \\sim C54-C53 \\sim C56-C55 \\sim C30-C31 \\sim C52-C37
 with sigma of 0.02
 C12-C13 \\sim C31-C32 \\sim C32-C14 \\sim C13-C14 \\sim C12-C31 \\sim C28-C11
\\sim C26-C10 \\sim C27-C26
 \\sim C27-C28 \\sim C44-C45 \\sim C48-C44 \\sim C48-C47 \\sim C46-C47 \\sim
C46-C45 \\sim C59-C51 \\sim C51-
 C52 \\sim C53-C52 \\sim C58-C53 \\sim C58-C59 \\sim C50-C49 \\sim C50-C39
\\sim C39-C40 \\sim C40-C41 ~
 C49-C41 \\sim C5-C6 \\sim C22-C6 \\sim C21-C22 \\sim C20-C21 \\sim C20-C5
\\sim C18-C19 \\sim C38-C19 ~
 C37-C38 \\sim C37-C36 \\sim C36-C18 \\sim C34-C35 \\sim C54-C35 \\sim C55-C54
\\sim C55-C33 \\sim C10-C11
 \\sim C33-C34 \\sim C7-C2 \\sim C1-C2 \\sim C9-C1 \\sim C8-C9 \\sim C8-C7
\\sim C42-C23 \\sim C23-C24 \\sim C25-
 C24 \\sim C43-C25 \\sim C42-C43 \\sim C4-C3 \\sim C17-C4 \\sim C16-C17 \\sim
C15-C16 \\sim C15-C3 \\sim C30-
 C56 \\sim C57-C56 \\sim C60-C57 \\sim C60-C29 \\sim C29-C30
 with sigma of 0.02
 C321-C322 \\sim C322-C323 \\sim C323-C324 \\sim C324-C325 \\sim C325-C326
\\sim C326-C321
 with sigma of 0.02
 C321-C325 \\sim C321-C323 \\sim C326-C324 \\sim C322-C326 \\sim C323-C325
\\sim C322-C324
 with sigma of 0.04
 C258-C259 \\sim C259-C260 \\sim C260-C261 \\sim C261-C262 \\sim C262-C263
\\sim C263-C258
 with sigma of 0.02
 C258-C262 \\sim C258-C260 \\sim C263-C261 \\sim C259-C263 \\sim C260-C262
\\sim C259-C261
 with sigma of 0.04
 C257-C263 \\sim C257-C259
 with sigma of 0.04
 O343-C342 \\sim O341-C342
 with sigma of 0.02
 C163-C160 \\sim C157-C156 \\sim C153-C152
 with sigma of 0.02
 C231-C228 \\sim C225-C224 \\sim C237-C234 \\sim C221-C220 \\sim C217-C214
\\sim C211-C210 \\sim C207-
 C206 \\sim C203-C200 \\sim C197-C196
 with sigma of 0.02
 C125-C124 \\sim C129-C128 \\sim C133-C132 \\sim C139-C136 \\sim C143-C142
\\sim C149-C146 \\sim C153-
 C152 \\sim C157-C156 \\sim C163-C160
 with sigma of 0.02
3. Restrained planarity
 C320, C321, C322, C323, C324, C325, C326
 with sigma of 0.1
 C257, C258, C259, C260, C261, C262, C263
 with sigma of 0.1
 C122, C188, C187, C186, C185, C123
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.03 and sigma
for terminal atoms of 0.06
Uanis(C202) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C139) \\sim Ueq, Uanis(C136) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C56) = Uanis(C47)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{C306, C308, C309, C307, C310, C312, C311} sigma for 1-2: 0.02, 1-3: 0.02
as in
{C299, C301, C302, C300, C303, C305, C304}
7. Others
 Sof(C327)=Sof(H32D)=Sof(H32E)=Sof(H32F)=Sof(C329)=Sof(H329)=Sof(C330)=
 Sof(H330)=Sof(C331)=Sof(H331)=Sof(C332)=Sof(H332)=Sof(C333)=Sof(H333)=
 Sof(C328)=1-FVAR(1)
 Sof(C320)=Sof(H32A)=Sof(H32B)=Sof(H32C)=Sof(C321)=Sof(C322)=Sof(H322)=
 Sof(C323)=Sof(H323)=Sof(C324)=Sof(H324)=Sof(C325)=Sof(H325)=Sof(C326)=
 Sof(H326)=FVAR(1)
 Sof(C299)=Sof(H29D)=Sof(H29E)=Sof(H29F)=Sof(C301)=Sof(H301)=Sof(C302)=
 Sof(H302)=Sof(C300)=Sof(C303)=Sof(H303)=Sof(C305)=Sof(H305)=Sof(C304)=
 Sof(H304)=1-FVAR(2)
 Sof(C306)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C308)=Sof(H308)=Sof(C309)=
 Sof(H309)=Sof(C307)=Sof(C310)=Sof(H310)=Sof(C312)=Sof(H312)=Sof(C311)=
 Sof(H311)=FVAR(2)
8.a Riding coordinates:
 O362(H362), C320(H32A,H32B,H32C), C327(H32D,H32E,H32F), C299(H29D,H29E,H29F)
8.b Aromatic/amide H refined with riding coordinates:
 C205(H205), C223(H223), C192(H192), C130(H130), C131(H131), C175(H175),
 C176(H176), C147(H147), C145(H145), C194(H194), C155(H155), C162(H162),
 C126(H126), C252(H252), C184(H184), C213(H213), C227(H227), C209(H209),
 C219(H219), C183(H183), C298(H298), C178(H178), C138(H138), C270(H270),
 C308(H308), C309(H309), C310(H310), C312(H312), C311(H311), C226(H226),
 C238(H238), C212(H212), C254(H254), C233(H233), C182(H182), C208(H208),
 C253(H253), C232(H232), C154(H154), C294(H294), C137(H137), C255(H255),
 C242(H242), C241(H241), C222(H222), C243(H243), C215(H215), C204(H204),
 C127(H127), C266(H266), C168(H168), C165(H165), C150(H150), C151(H151),
 C171(H171), C172(H172), C283(H283), C282(H282), C281(H281), C280(H280),
 C284(H284), C239(H239), C174(H174), C185(H185), C173(H173), C169(H169),
 C199(H199), C201(H201), C202(H202), C198(H198), C229(H229), C193(H193),
 C195(H195), C161(H161), C144(H144), C230(H230), C295(H295), C187(H187),
 C277(H277), C276(H276), C275(H275), C274(H274), C273(H273), C167(H167),
 C247(H247), C244(H244), C268(H268), C245(H245), C170(H170), C181(H181),
 C177(H177), C186(H186), C235(H235), C148(H148), C269(H269), C249(H249),
 C218(H218), C236(H236), C246(H246), C267(H267), C135(H135), C141(H141),
 C248(H248), C250(H250), C159(H159), C158(H158), C140(H140), C164(H164),
 C188(H188), C291(H291), C290(H290), C289(H289), C288(H288), C287(H287),
 C297(H297), C296(H296), C216(H216), C134(H134), C322(H322), C323(H323),
 C324(H324), C325(H325), C326(H326), C259(H259), C263(H263), C260(H260),
 C262(H262), C261(H261), C329(H329), C330(H330), C331(H331), C332(H332),
 C333(H333), C301(H301), C302(H302), C303(H303), C305(H305), C304(H304)
8.c Fitted pentagon refined as free rotating group:
 C13(C14,C32,C31,C12), C50(C49,C41,C40,C39)
8.d Fitted hexagon refined as free rotating group:
 C130(C131,C132,C175,C176,C129), C150(C151,C152,C171,C172,C149), C283(C282,
 C281,C280,C279,C284), C199(C200,C201,C202,C197,C198), C272(C277,C276,C275,C274,
 C273), C286(C291,C290,C289,C288,C287), C329(C330,C331,C332,C333,C328)
8.e Tetrahedral OH refined with riding coordinates:
 O343(H343), O336(H336), O357(H357)
8.f Idealised Me refined as rotating group:
 C306(H30A,H30B,H30C), C264(H26A,H26B,H26C), C292(H29A,H29B,H29C), C278(H27A,
 H27B,H27C), C285(H28A,H28B,H28C), C271(H27D,H27E,H27F), C257(H25A,H25B,H25C)
;
_shelx_res_checksum              32750
_olex2_submission_special_instructions 'No special instructions were received'