Planar chiral orange-red TADF materials with AIE properties for efficient circularly polarized OLEDs.
Xiao, Xiong; Liang, Jia-Qi; Hu, Jia-Jun; Yuan, Li; Zhu, Jia-Zhen; Chen, Zong-Ju; Song, You; Li, Cheng-Hui; Zheng, You-Xuan; Chemical communications (Cambridge, England) 61 (2025) 11766–11769; doi:10.1039/d5cc02694f

data_7134782
_publ_section_title
;
 Planar chiral orange-red TADF materials with AIE properties for efficient
 circularly polarized OLEDs.
;
_journal_issue                   63
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11766
_journal_page_last               11769
_journal_paper_doi               10.1039/d5cc02694f
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C92 H84 N6, C H2 Cl2'
_chemical_formula_sum            'C93 H86 Cl2 N6'
_chemical_formula_weight         1358.57
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-06-05
_audit_creation_method
;
Olex2 1.5
(compiled 2025.05.22 svn.r631f81ec for OlexSys, GUI svn.r7248)
;
_audit_update_record
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2025-06-05 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8363(7)
_cell_length_b                   15.8363(7)
_cell_length_c                   58.867(4)
_cell_measurement_reflns_used    9820
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      73.327
_cell_measurement_theta_min      2.889
_cell_volume                     14763.2(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       73
_diffrn_reflns_limit_l_min       -71
_diffrn_reflns_number            220544
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.473
_diffrn_reflns_theta_min         2.889
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.189
_exptl_absorpt_correction_T_max  0.1738
_exptl_absorpt_correction_T_min  0.0674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1347 before and 0.0688 after correction.
The Ratio of minimum to maximum transmission is 0.3878.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       block
_exptl_crystal_F_000             5760
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 5238 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     950
_refine_ls_number_reflns         15188
_refine_ls_number_restraints     88
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.7377P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                13341
_reflns_number_total             15188
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02694f2.cif
_cod_data_source_block           cu_20240914wq_lch_0m
_cod_depositor_comments
'Adding full bibliography for 7134782--7134784.cif.'
_cod_original_cell_volume        14763.1(17)
_cod_database_code               7134782
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.861
_olex2_refinement_description
;
1. Restrained distances
 Cl2-C93 \\sim Cl2A-C93A \\sim Cl1A-C93A \\sim Cl1-C93
 with sigma of 0.02
 C33-C32 \\sim C34-C33 \\sim C35-C34 \\sim C36-C35 \\sim C37-C36 \\sim C37-C32
 with sigma of 0.01
2. Rigid bond restraints
 C32, C33
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim Cl2 \\sim C93 \\sim Cl1A \\sim Cl2A \\sim C93A: within 2A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 2A
4. Others
 Sof(Cl1A)=Sof(Cl2A)=Sof(C93A)=Sof(H93C)=Sof(H93D)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(C93)=Sof(H93A)=Sof(H93B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C31(H31A,H31B), C38(H38A,H38B), C39(H39A,H39B), C63(H63A,
 H63B), C64(H64A,H64B), C69(H69A,H69B), C70(H70A,H70B), C93(H93A,H93B),
 C93A(H93C,H93D)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C18(H18), C23(H23), C24(H24),
 C25(H25), C26(H26), C33(H33), C34(H34), C36(H36), C37(H37), C41(H41), C42(H42),
  C52(H52), C53(H53), C54(H54), C55(H55), C60(H60), C61(H61), C66(H66),
 C67(H67), C71(H71), C72(H72), C74(H74), C75(H75), C77(H77), C80(H80), C82(H82),
  C83(H83)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C86(H86A,H86B,H86C), C87(H87A,
 H87B,H87C), C88(H88A,H88B,H88C), C90(H90A,H90B,H90C), C91(H91A,H91B,H91C),
 C92(H92A,H92B,H92C)
;
_shelx_res_checksum              96493
_shelx_hkl_checksum              97225
_olex2_submission_special_instructions 'No special instructions were received'