Aggregation caused quenching to aggregation induced emission transformation: a precise tuning based on BN-doped polycyclic aromatic hydrocarbons toward subcellular organelle specific imaging
Huang, Huanan; Liu, Lingxiu; Wang, Jianguo; Zhou, Ying; Hu, Huanan; Ye, Xinglin; Liu, Guochang; Xu, Zhixiong; Xu, Han; Yang, Wen; Wang, Yawei; Peng, You; Yang, Pinghua; Sun, Jianqi; Yan, Ping; Cao, Xiaohua; Tang, Ben Zhong; Chemical Science  (2022) –; doi:10.1039/D2SC00380E

data_1566351
_publ_section_title
;
 Aggregation caused quenching to aggregation induced emission
 transformation: a precise tuning based on BN-doped polycyclic aromatic
 hydrocarbons toward subcellular organelle specific imaging
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00380E
_journal_year                    2022
_chemical_formula_moiety         'C32 H23 B N2'
_chemical_formula_sum            'C32 H23 B N2'
_chemical_formula_weight         446.33
_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     dual
_audit_creation_date             2021-02-19
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6270)
;
_audit_update_record
;
2021-07-25 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.688(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1281(4)
_cell_length_b                   14.6359(10)
_cell_length_c                   22.9977(13)
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.5890
_cell_measurement_theta_min      2.9990
_cell_volume                     2730.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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      4.00  82.00   1.00    1.00    --   40.73 -99.00 120.00   78
  2  \w     56.00 140.00   1.00    2.00    --  107.58 -77.00  30.00   84
  3  \w     55.00  88.00   1.00    1.00    --   40.73-125.00 -90.00   33
  4  \w     26.00  98.00   1.00    2.00    --  107.58 -94.00 -60.00   72
  5  \w    118.00 174.00   1.00    2.00    --  107.58  45.00  90.00   56
  6  \w    115.00 154.00   1.00    2.00    --  107.58 125.00  90.00   39
  7  \w    148.00 178.00   1.00    2.00    --  107.58 125.00 120.00   30
  8  \w    104.00 146.00   1.00    2.00    --  107.58 104.00  27.00   42
  9  \w     85.00 116.00   1.00    2.00    --  107.58  45.00  90.00   31
 10  \w     78.00 178.00   1.00    2.00    --  107.58  61.00-180.00  100
 11  \w   -120.00  -5.00   1.00    1.00    --  -40.73 -19.00-120.00  115
;
_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      -0.0805241000
_diffrn_orient_matrix_UB_12      0.0937709000
_diffrn_orient_matrix_UB_13      -0.0127970000
_diffrn_orient_matrix_UB_21      -0.0882054000
_diffrn_orient_matrix_UB_22      -0.0387605000
_diffrn_orient_matrix_UB_23      -0.0559269000
_diffrn_orient_matrix_UB_31      -0.1478153000
_diffrn_orient_matrix_UB_32      -0.0278774000
_diffrn_orient_matrix_UB_33      0.0348134000
_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  0.0251
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10196
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         3.582
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (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    1.086
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4826
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0933
_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^)+(0.1321P)^2^+2.7093P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2568
_refine_ls_wR_factor_ref         0.2696
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3888
_reflns_number_total             4826
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00380e3.cif
_cod_data_source_block           yang02-0219
_cod_database_code               1566351
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.936
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid bond restraints
 C5, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C4 \\sim C5: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
  C14(H14), C17(H17), C18(H18), C20(H20), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              99506
_shelx_hkl_checksum              51556
_shelx_fab_checksum              37255
_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 1.907
_oxdiff_exptl_absorpt_empirical_full_min 0.401