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_7134783
_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         'C76 H52 N6, 2(C H2 Cl2)'
_chemical_formula_sum            'C78 H56 Cl4 N6'
_chemical_formula_weight         1219.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
;
2025-06-05 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.456(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5469(10)
_cell_length_b                   23.8140(14)
_cell_length_c                   19.6420(12)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      25.314
_cell_measurement_theta_min      2.258
_cell_volume                     6010.7(7)
_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      193.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            46429
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.382
_diffrn_reflns_theta_min         1.801
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.0916
_exptl_absorpt_correction_T_min  0.0634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1119 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.6921.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             2536
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.932
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1011
_refine_ls_number_reflns         11012
_refine_ls_number_restraints     718
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0760
_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^)+(0.0981P)^2^+7.3358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1930
_refine_ls_wR_factor_ref         0.2268
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7229
_reflns_number_total             11012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02694f2.cif
_cod_data_source_block           240919lu_lch_5_0m
_cod_depositor_comments
'Adding full bibliography for 7134782--7134784.cif.'
_cod_database_code               7134783
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Restrained distances
 Cl2A-Cl1A
 2.9 with sigma of 0.02
 Cl3-C78 \\sim Cl3A-C78A
 with sigma of 0.02
 Cl4-C78 \\sim Cl4A-C78A
 with sigma of 0.02
 Cl3-Cl4 \\sim Cl3A-Cl4A
 with sigma of 0.04
 C9-C8 \\sim C9-C8A
 with sigma of 0.02
 C13-C14 \\sim C13-C14A
 with sigma of 0.02
 C2-C1 \\sim C2A-C1A
 with sigma of 0.02
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C2-C14 \\sim C2A-C14A
 with sigma of 0.02
 C8-C7 \\sim C8A-C7A
 with sigma of 0.02
 C6-C5 \\sim C6A-C5A
 with sigma of 0.02
 C6-C1 \\sim C6A-C1A
 with sigma of 0.02
 C5-C4 \\sim C5A-C4A
 with sigma of 0.02
 C5-C7 \\sim C5A-C7A
 with sigma of 0.02
 C3-C4 \\sim C3A-C4A
 with sigma of 0.02
 C9-C7 \\sim C9-C7A
 with sigma of 0.04
 C13-C2 \\sim C13-C2A
 with sigma of 0.04
 C2-C6 \\sim C2A-C6A
 with sigma of 0.04
 C2-C4 \\sim C2A-C4A
 with sigma of 0.04
 C8-C5 \\sim C8A-C5A
 with sigma of 0.04
 C6-C4 \\sim C6A-C4A
 with sigma of 0.04
 C6-C7 \\sim C6A-C7A
 with sigma of 0.04
 C5-C1 \\sim C5A-C1A
 with sigma of 0.04
 C5-C3 \\sim C5A-C3A
 with sigma of 0.04
 C1-C3 \\sim C1A-C3A
 with sigma of 0.04
 C1-C14 \\sim C1A-C14A
 with sigma of 0.04
 C3-C14 \\sim C3A-C14A
 with sigma of 0.04
 C4-C7 \\sim C4A-C7A
 with sigma of 0.04
 C38-C39 \\sim C38-C39A
 with sigma of 0.02
 C39-C40 \\sim C39A-C40A
 with sigma of 0.02
 C41-C42 \\sim C41A-C42A
 with sigma of 0.02
 C41-C48 \\sim C41A-C48A
 with sigma of 0.02
 C41-C40 \\sim C41A-C40A
 with sigma of 0.02
 C46-C45 \\sim C46-C45A
 with sigma of 0.02
 C47-C48 \\sim C47A-C48A
 with sigma of 0.02
 C47-C44 \\sim C47A-C44A
 with sigma of 0.02
 C42-C43 \\sim C42A-C43A
 with sigma of 0.02
 C44-C43 \\sim C44A-C43A
 with sigma of 0.02
 C44-C45 \\sim C44A-C45A
 with sigma of 0.02
 C38-C40 \\sim C38-C40A
 with sigma of 0.04
 C39-C41 \\sim C39A-C41A
 with sigma of 0.04
 C41-C47 \\sim C41A-C47A
 with sigma of 0.04
 C41-C43 \\sim C41A-C43A
 with sigma of 0.04
 C46-C44 \\sim C46-C44A
 with sigma of 0.04
 C47-C43 \\sim C47A-C43A
 with sigma of 0.04
 C47-C45 \\sim C47A-C45A
 with sigma of 0.04
 C42-C48 \\sim C42A-C48A
 with sigma of 0.04
 C42-C44 \\sim C42A-C44A
 with sigma of 0.04
 C42-C40 \\sim C42A-C40A
 with sigma of 0.04
 C48-C44 \\sim C48A-C44A
 with sigma of 0.04
 C48-C40 \\sim C48A-C40A
 with sigma of 0.04
 C43-C45 \\sim C43A-C45A
 with sigma of 0.04
 Cl2A-C77A \\sim Cl1-C77 \\sim Cl1A-C77A \\sim Cl2-C77
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Cl3 \\sim Cl4 \\sim C78 \\sim Cl3A \\sim Cl4A \\sim C78A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C14
\\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim C7A \\sim C8A
\\sim C14A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
C39 \\sim C40 \\sim C41 \\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C47 \\sim
C48 \\sim C39A \\sim C40A \\sim C41A \\sim C42A \\sim C43A \\sim C44A \\sim
C45A \\sim C47A \\sim C48A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
Cl1 \\sim Cl2 \\sim C77 \\sim Cl1A \\sim Cl2A \\sim C77A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Others
 Sof(H13C)=Sof(H13D)=Sof(H46C)=Sof(H46D)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(C3A)=
 Sof(H3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7AA)=
 Sof(H7AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C39A)=
 Sof(H39C)=Sof(H39D)=Sof(C40A)=Sof(H40C)=Sof(H40D)=Sof(C41A)=Sof(C42A)=
 Sof(H42A)=Sof(C43A)=Sof(H43A)=Sof(C44A)=Sof(C45A)=Sof(H45C)=Sof(H45D)=
 Sof(C47A)=Sof(H47A)=Sof(C48A)=Sof(H48A)=Sof(Cl3A)=Sof(Cl4A)=Sof(C78A)=
 Sof(H78C)=Sof(H78D)=1-FVAR(1)
 Sof(H13A)=Sof(H13B)=Sof(H46A)=Sof(H46B)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(C3)=
 Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7A)=Sof(H7B)=
 Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C39)=Sof(H39A)=
 Sof(H39B)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(C41)=Sof(C42)=Sof(H42)=Sof(C43)=
 Sof(H43)=Sof(C44)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(C47)=Sof(H47)=Sof(C48)=
 Sof(H48)=Sof(Cl3)=Sof(Cl4)=Sof(C78)=Sof(H78B)=Sof(H78A)=FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C77A)=Sof(H77C)=Sof(H77D)=1-FVAR(2)
 Sof(Cl1)=Sof(Cl2)=Sof(C77)=Sof(H77A)=Sof(H77B)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C13(H13C,H13D), C46(H46A,H46B), C46(H46C,H46D), C7(H7A,H7B),
 C8(H8A,H8B), C14(H14A,H14B), C39(H39A,H39B), C40(H40A,H40B), C45(H45A,H45B),
 C7A(H7AA,H7AB), C8A(H8AA,H8AB), C14A(H14C,H14D), C39A(H39C,H39D), C40A(H40C,
 H40D), C45A(H45C,H45D), C77(H77A,H77B), C77A(H77C,H77D), C78(H78B,H78A),
 C78A(H78C,H78D)
4.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C36(H36),
 C37(H37), C49(H49), C50(H50), C51(H51), C52(H52), C56(H56), C57(H57), C58(H58),
  C59(H59), C61(H61), C62(H62), C63(H63), C64(H64), C65(H65), C66(H66),
 C67(H67), C71(H71), C72(H72), C73(H73), C74(H74), C76(H76), C1(H1), C3(H3),
 C4(H4), C6(H6), C42(H42), C43(H43), C47(H47), C48(H48), C1A(H1A), C3A(H3A),
 C4A(H4A), C6A(H6A), C42A(H42A), C43A(H43A), C47A(H47A), C48A(H48A)
;
_shelx_res_checksum              24342
_shelx_hkl_checksum              32030
_olex2_submission_special_instructions 'No special instructions were received'