Base-Assisted One-Pot Synthesis of N,N',N"-Triaryltriazatriangulenium Dyes: Enhanced Fluorescence Efficiency by Steric Constraints
Peter Hammershøj; Thomas Just Sørensen; Bao-Hang Han; Bo W. Laursen; Journal of Organic Chemistry 77 (2012) 5606–5612; doi:10.1021/jo3007732

data_4027273
_publ_section_title
;
 Base-Assisted One-Pot Synthesis of N,N',N"-Triaryltriazatriangulenium
 Dyes: Enhanced Fluorescence Efficiency by Steric Constraints
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5606
_journal_page_last               5612
_journal_paper_doi               10.1021/jo3007732
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C37 H21 B Br3 F4 N3'
_chemical_formula_sum            'C37 H21 B Br3 F4 N3'
_chemical_formula_weight         834.11
_chemical_melting_point          573
_chemical_name_common            4-bromophenyl-TATA
_chemical_name_systematic
;
4,8,12-Tris(4-bromophenyl)-4,8,12-triazatriangulenium Tetrafluoroborate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(7)
_cell_angle_beta                 101.562(16)
_cell_angle_gamma                90.000(11)
_cell_formula_units_Z            4
_cell_length_a                   14.5170(17)
_cell_length_b                   10.9430(18)
_cell_length_c                   19.6690(18)
_cell_measurement_reflns_used    23947
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      1.43
_cell_volume                     3061.2(7)
_computing_cell_refinement       'COLLECT (Nonius, 1999)'
_computing_data_collection       'EvalCCD (duisenbeg, 2003)'
_computing_data_reduction        'EvalCCD (Duisenberg, 2003)'
_computing_molecular_graphics    mercury
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      122(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1431
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            73917
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    4.013
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            reed
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_description       needles
_exptl_crystal_F_000             1640
_exptl_crystal_preparation       Toluene/dicloromethane
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         4.734
_refine_diff_density_min         -2.131
_refine_diff_density_rms         0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.438
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         8955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.438
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1852
_refine_ls_wR_factor_ref         0.2135
_reflns_number_gt                6485
_reflns_number_total             8955
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3007732_si_002_2.cif
_cod_data_source_block           compound_4
_cod_database_code               4027273