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_1566350
_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         'C36 H33 B N4'
_chemical_formula_sum            'C36 H33 B N4'
_chemical_formula_weight         532.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-02-03
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-07-25 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.494(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3480(15)
_cell_length_b                   9.7155(7)
_cell_length_c                   20.1083(19)
_cell_measurement_reflns_used    2236
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.8490
_cell_measurement_theta_min      3.9720
_cell_volume                     2790.2(4)
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -62.00  21.00   1.00   10.00    --  -40.73  38.00  30.00   83
  2  \w     43.00  95.00   1.00   10.00    --   40.73-125.00  60.00   52
  3  \w     30.00 108.00   1.00   15.00    --  107.58 -94.00  60.00   78
  4  \w     37.00 131.00   1.00   15.00    --  107.58 -45.00  30.00   94
  5  \w     79.00 178.00   1.00   15.00    --  107.58  30.00  60.00   99
  6  \w    107.00 134.00   1.00   15.00    --  107.58 125.00 -60.00   27
  7  \w     41.00 133.00   1.00   15.00    --  107.58 -45.00-120.00   92
  8  \w     43.00  96.00   1.00   15.00    --  107.58 -94.00 -90.00   53
  9  \w   -112.00 -12.00   1.00   10.00    --  -40.73 -77.00-120.00  100
;
_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      -0.0373403000
_diffrn_orient_matrix_UB_12      0.0233574000
_diffrn_orient_matrix_UB_13      -0.0735416000
_diffrn_orient_matrix_UB_21      0.0932925000
_diffrn_orient_matrix_UB_22      -0.0530727000
_diffrn_orient_matrix_UB_23      -0.0224534000
_diffrn_orient_matrix_UB_31      -0.0393564000
_diffrn_orient_matrix_UB_32      -0.1474757000
_diffrn_orient_matrix_UB_33      -0.0035266000
_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  0.0560
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4941
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         3.626
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58119
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         4941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1400
_refine_ls_R_factor_gt           0.1150
_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^)+(0.1087P)^2^+11.1146P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3236
_refine_ls_wR_factor_ref         0.3393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3513
_reflns_number_total             4941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00380e3.cif
_cod_data_source_block           yang01
_cod_database_code               1566350
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.654(7)
 0.346(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25), C26(H26),
  C30(H30), C31(H31), C33(H33), C34(H34)
3.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C)
;
_shelx_res_checksum              55081
_shelx_hkl_checksum              47638
_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 1.644
_oxdiff_exptl_absorpt_empirical_full_min 0.434