Chirality-activated mechanoluminescence from aggregation-induced emission enantiomers with high contrast mechanochromism and force-induced delayed fluorescence
Chen, Yitong; Xu, Chao; Xu, Bingjia; Mao, Zhu; Li, Jian-An; Yang, Zhan; Peethani, Naga Raju; Liu, Cong; Shi, Guang; Gu, Feng Long; Zhang, Yi; Chi, Zhenguo; Materials Chemistry Frontiers 3 (2019) 1800–; doi:10.1039/C9QM00312F

data_1554676
_publ_section_title
;
 Chirality-activated mechanoluminescence from aggregation-induced emission
 enantiomers with high contrast mechanochromism and force-induced delayed
 fluorescence
;
_journal_issue                   9
_journal_name_full               'Materials Chemistry Frontiers'
_journal_page_first              1800
_journal_paper_doi               10.1039/C9QM00312F
_journal_volume                  3
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H22 N2 O2 S'
_chemical_formula_sum            'C30 H22 N2 O2 S'
_chemical_formula_weight         474.55
_chemical_name_systematic        (R)-ImNT
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-27 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                85.684(2)
_cell_angle_beta                 78.373(2)
_cell_angle_gamma                89.276(2)
_cell_formula_units_Z            4
_cell_length_a                   12.1382(2)
_cell_length_b                   12.8179(3)
_cell_length_c                   15.1854(3)
_cell_measurement_reflns_used    18649
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      62.9680
_cell_measurement_theta_min      3.7060
_cell_volume                     2307.59(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 21.1652
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -44.00  46.00   1.00    3.00    --   22.00 -52.00 -23.10   90
  2  \w     20.00 110.00   1.00   12.00    --   83.03 -77.00 -90.00   90
  3  \w     32.00 122.00   1.00   12.00    --   83.03-125.00  90.00   90
  4  \w     34.00 110.00   1.00   12.00    --   83.03 -77.00 150.00   76
  5  \w     20.00  93.00   1.00   12.00    --   83.03 -57.00  60.00   73
  6  \w     19.00  44.00   1.00   12.00    --   50.00  79.00 -66.89   25
  7  \w     33.00  59.00   1.00   12.00    --   62.00  77.00 -44.16   26
  8  \w     54.00  81.00   1.00   12.00    --   83.03  77.00 -60.00   27
  9  \w     93.00 149.00   1.00   12.00    --   83.03  77.00 -60.00   56
 10  \w     96.00 142.00   1.00   12.00    --   83.03  77.00-150.00   46
 11  \w     94.00 125.00   1.00   12.00    --   54.00  76.00-162.79   31
 12  \w     92.00 141.00   1.00   12.00    --   83.03  77.00-180.00   49
 13  \w     94.00 136.00   1.00   12.00    --   83.03  77.00-120.00   42
 14  \w     99.00 152.00   1.00   12.00    --   83.03  77.00 -30.00   53
 15  \w     98.00 130.00   1.00   12.00    --   83.03  77.00  60.00   32
 16  \w    102.00 144.00   1.00   12.00    --   83.03 125.00 120.00   42
 17  \w     94.00 154.00   1.00   12.00    --   83.03  77.00  30.00   60
 18  \w     96.00 123.00   1.00   12.00    --   83.03  77.00 150.00   27
 19  \w     94.00 152.00   1.00   12.00    --   83.03  77.00 120.00   58
 20  \w     54.00  82.00   1.00   12.00    --   83.03  77.00  60.00   28
 21  \w     53.00  79.00   1.00   12.00    --   83.03  77.00  30.00   26
 22  \w     53.00 154.00   1.00   12.00    --   83.03  77.00   0.00  101
 23  \w     92.00 146.00   1.00   12.00    --   83.03  77.00 -90.00   54
 24  \w     54.00  81.00   1.00   12.00    --   83.03  77.00 -30.00   27
 25  \w     53.00  82.00   1.00   12.00    --   83.03  77.00 -90.00   29
 26  \w     53.00  80.00   1.00   12.00    --   83.03  77.00-150.00   27
 27  \w     53.00  84.00   1.00   12.00    --   83.03  77.00-180.00   31
 28  \w     53.00  84.00   1.00   12.00    --   83.03  77.00-120.00   31
 29  \w     32.00  62.00   1.00   12.00    --   62.00  75.00 -99.01   30
 30  \w     27.00  67.00   1.00   12.00    --   54.00  76.00-162.79   40
 31  \w     32.00  65.00   1.00   12.00    --   62.00  75.00-135.06   33
 32  \w     18.00  43.00   1.00   12.00    --   50.00  82.00-177.25   25
 33  \w    -14.00  71.00   1.00    3.00    --    0.00  37.00-180.00   85
 34  \w      1.00  47.00   1.00    3.00    --   22.00 -58.00-175.68   46
 35  \w     36.00  62.00   1.00   12.00    --   66.00  77.00 -20.43   26
 36  \w     37.00  62.00   1.00   12.00    --   66.00  77.00   4.37   25
 37  \w     36.00  72.00   1.00   12.00    --   66.00  76.00  36.75   36
 38  \w     53.00 153.00   1.00   12.00    --   83.03  77.00  90.00  100
 39  \w     53.00  83.00   1.00   12.00    --   83.03  77.00 150.00   30
 40  \w     53.00  80.00   1.00   12.00    --   83.03  77.00 120.00   27
 41  \w     41.00  66.00   1.00   12.00    --   70.00  77.00 107.71   25
 42  \w     37.00  64.00   1.00   12.00    --   66.00  75.00 146.25   27
 43  \w     36.00  70.00   1.00   12.00    --   66.00  75.00  87.56   34
 44  \w     18.00  44.00   1.00   12.00    --   50.00  82.00 108.82   26
 45  \w     14.00  39.00   1.00   12.00    --   46.00  83.00  49.94   25
 46  \w     14.00  39.00   1.00   12.00    --   46.00  83.00 -21.43   25
 47  \w    -25.00   0.00   1.00    3.00    --   26.00 120.00 -91.47   25
 48  \w    -30.00  -5.00   1.00    3.00    --   22.00 126.00  85.63   25
 49  \w    -56.00  19.00   1.00    3.00    --    0.00 -57.00  90.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1203113000
_diffrn_orient_matrix_UB_12      -0.0242205000
_diffrn_orient_matrix_UB_13      0.0527595000
_diffrn_orient_matrix_UB_21      0.0190218000
_diffrn_orient_matrix_UB_22      0.0699599000
_diffrn_orient_matrix_UB_23      0.0737778000
_diffrn_orient_matrix_UB_31      -0.0442014000
_diffrn_orient_matrix_UB_32      0.0951132000
_diffrn_orient_matrix_UB_33      -0.0506031000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30459
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        62.847
_diffrn_reflns_theta_max         62.847
_diffrn_reflns_theta_min         3.458
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.497
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 6107 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1261
_refine_ls_number_reflns         14132
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0798P)^2^+3.4627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1442
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                13566
_reflns_number_total             14132
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qm00312f4.cif
_cod_data_source_block           (R)-ImNT
_cod_database_code               1554676
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHONS
_chemical_oxdiff_usercomment     R-ImNT
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C01B(H01B), C01R(H01R), C02A(H02D), C030(H030)
2.b Secondary CH2 refined with riding coordinates:
 C02D(H02F,H02G), C02Z(H02A,H02B), C031(H03Y,H), C03D(H03A,H03B), C03F(H03N,
 H03O), C03I(H03,HA), C03J(H0AA,HB), C03N(H03G,H03H), C03Q(H03W,H03X),
 C03S(H03I,H03J), C03T(H03C,H03D), C03W(H03K,H03L)
2.c Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C011(H011), C012(H012), C014(H014), C016(H016), C018(H018),
 C01D(H01D), C01E(H01E), C01G(H01G), C01L(H01L), C01O(H01O), C01Q(H01Q),
 C01T(H01T), C01U(H01U), C01X(H01X), C01Y(H01Y), C020(H020), C021(H021),
 C023(H023), C026(H026), C027(H027), C028(H028), C029(H029), C02B(H02C),
 C02C(H02E), C02G(H02H), C02H(H02I), C02I(H02J), C02K(H02K), C02M(H02M),
 C02N(H02N), C02O(H02O), C02P(H02P), C02Q(H02Q), C02R(H02R), C02S(H02S),
 C02U(H02U), C02V(H02V), C02W(H02W), C02X(H02X), C032(H032), C033(H033),
 C034(H034), C035(H035), C036(H036), C037(H037), C038(H038), C039(H039),
 C03A(H03E), C03C(H03F), C03E(H03Z), C03G(H03Q), C03K(H1AA), C03L(H03S),
 C03M(H03M), C03O(H03T), C03P(H03P), C03R(H03R), C03U(H03U), C03V(H03V)
;
_olex2_date_sample_data_collection 2018-06-07
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.843
_oxdiff_exptl_absorpt_empirical_full_min 0.695