New n-Type Organic Semiconductors: Synthesis, Single Crystal Structures, Cyclic Voltammetry, Photophysics, Electron Transport, and Electroluminescence of a Series of Diphenylanthrazolines
Christopher J. Tonzola; Maksudul M. Alam; Werner Kaminsky; Samson A. Jenekhe; Journal of the American Chemical Society 125 (2003) 13548–13558; doi:10.1021/ja036314e

data_4114306
_publ_contact_author
;
      Tonzola, Chris
    Department of Chemistry, BOX 351700
    University of Washington
    Seattle, WA 98195
    USA
;
_publ_contact_author_email       cjt@u.washington.edu
_publ_section_title
;
 New n-Type Organic Semiconductors: Synthesis, Single Crystal Structures,
 Cyclic Voltammetry, Photophysics, Electron Transport, and
 Electroluminescence of a Series of Diphenylanthrazolines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13548
_journal_page_last               13558
_journal_paper_doi               10.1021/ja036314e
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C44 H38 N2'
_chemical_formula_sum            'C44 H38 N2'
_chemical_formula_weight         594.76
_chemical_melting_point          629
_chemical_name_common
;
2,7-Bis(4'-tert-butylphenyl)-4,9-diphenylanthrazoline
;
_chemical_name_systematic
;
2,7-Bis(4'-tert-butylphenyl)-4,9-diphenylanthrazoline
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.7610(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.8400(8)
_cell_length_b                   5.9620(2)
_cell_length_c                   22.5290(10)
_cell_measurement_reflns_used    1958
_cell_measurement_temperature    130(2)
_cell_volume                     3195.2(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        DENZO
_computing_molecular_graphics    'maXus, Zortep'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3442
_diffrn_reflns_theta_full        22.21
_diffrn_reflns_theta_max         22.21
_diffrn_reflns_theta_min         3.77
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_correction_T_min  0.9322
_exptl_absorpt_correction_type   HKL-Scalepack
_exptl_absorpt_process_details   'Numeric, using data-redundancy'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0022(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         1918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.6400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                1528
_reflns_number_total             1918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja036314esi20030523_112506_1.cif
_cod_data_source_block           1c
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4114306