Achievement of efficient thermally activated delayed fluorescence materials based on 1,8-naphthalimide derivatives exhibiting piezochromic and thermochromic luminescence
Chen‡, Meiling; Chen‡, Yuzhuo; Su, Zhongzhen; Li, Yuchun; Fei, Hanxiao; Zhang, Hua; Wu, Yunan; RSC Advances 14 (2024) 17434–17439; doi:10.1039/D4RA02981J

data_7248747
_publ_section_title
;
 Achievement of efficient thermally activated delayed fluorescence
 materials based on 1,8-naphthalimide derivatives exhibiting piezochromic
 and thermochromic luminescence
;
_journal_issue                   25
_journal_name_full               'RSC Advances'
_journal_page_first              17434
_journal_page_last               17439
_journal_paper_doi               10.1039/D4RA02981J
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C36 H22 N2 O2, C H2 Cl2'
_chemical_formula_sum            'C37 H24 Cl2 N2 O2'
_chemical_formula_weight         599.48
_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
_audit_creation_date             2024-03-31
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-31 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.1790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.24880(10)
_cell_length_b                   13.19660(10)
_cell_length_c                   16.31220(10)
_cell_measurement_reflns_used    12329
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9470
_cell_measurement_theta_min      4.1460
_cell_volume                     2847.62(4)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5826
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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    -38.00 -13.00   1.00    2.00    --  -41.64 -77.00 -60.00   25
  2  \w    -55.00  33.00   1.00    2.00    --  -41.64  37.00  90.00   88
  3  \w     23.00  84.00   1.00    2.00    --   41.64-125.00 150.00   61
  4  \w     61.00 108.00   1.00    4.00    --  107.79 -94.00 120.00   47
  5  \w     40.00 133.00   1.00    4.00    --  107.79 -45.00  60.00   93
  6  \w     84.00 122.00   1.00    4.00    --  107.79-125.00 -60.00   38
  7  \w     37.00 100.00   1.00    4.00    --  107.79 -61.00-150.00   63
  8  \w     83.00 173.00   1.00    4.00    --  107.79  30.00-150.00   90
  9  \w    130.00 174.00   1.00    4.00    --  107.79 125.00 -30.00   44
 10  \w    142.00 171.00   1.00    4.00    --  107.79 125.00  90.00   29
 11  \w    123.00 174.00   1.00    4.00    --  107.79  61.00 150.00   51
 12  \w    121.00 177.00   1.00    4.00    --  107.79 125.00 120.00   56
 13  \w    107.00 132.00   1.00    4.00    --  107.79 125.00   0.00   25
 14  \w     94.00 128.00   1.00    4.00    --  107.79 125.00  90.00   34
 15  \w     91.00 118.00   1.00    4.00    --  107.79  61.00 150.00   27
 16  \w     90.00 176.00   1.00    4.00    --  107.79  45.00   0.00   86
 17  \w     96.00 159.00   1.00    4.00    --  107.79 125.00-150.00   63
 18  \w     29.00  96.00   1.00    2.00    --   41.64-125.00 -60.00   67
 19  \w     39.00 116.00   1.00    4.00    --  107.79-125.00  90.00   77
 20  \w   -118.00 -77.00   1.00    2.00    --  -41.64 -77.00 -60.00   41
 21  \w   -125.00  13.00   1.00    2.00    --  -41.64   0.00  60.00  138
;
_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      -0.0778908000
_diffrn_orient_matrix_UB_12      0.0584233000
_diffrn_orient_matrix_UB_13      0.0484159000
_diffrn_orient_matrix_UB_21      0.0257071000
_diffrn_orient_matrix_UB_22      0.0980106000
_diffrn_orient_matrix_UB_23      -0.0457023000
_diffrn_orient_matrix_UB_31      -0.0826590000
_diffrn_orient_matrix_UB_32      -0.0246364000
_diffrn_orient_matrix_UB_33      -0.0672043000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20667
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.156
_diffrn_reflns_theta_min         4.312
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80991
_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    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.857
_refine_diff_density_min         -1.531
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0757
_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^)+(0.1357P)^2^+5.2086P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2295
_refine_ls_wR_factor_ref         0.2324
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5331
_reflns_number_total             5703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02981j2.cif
_cod_data_source_block           17110904
_cod_database_code               7248747
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     mp
_shelx_estimated_absorpt_t_max   0.719
_shelx_estimated_absorpt_t_min   0.452
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H37a(0.75) H37b(0.75) H37c(0.25) H37d(0.25) Cl2(0.75) Cl3(0.25)
3.a Secondary CH2 refined with riding coordinates:
 C37(H37a,H37b), C37(H37c,H37d)
3.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C26(H26), C34(H34), C9(H9), C19(H19), C5(H5), C21(H21),
 C11(H11), C23(H23), C3(H3), C25(H25), C13(H13), C27(H27), C7(H7), C29(H29),
 C15(H15), C31(H31), C2(H2), C33(H33), C17(H17), C35(H35)
;
_shelx_res_checksum              61933
_shelx_hkl_checksum              54859
_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 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.666