Orbital-Energy Modulation of Tetrabenzoporphyrin-Derived Non-Fullerene Acceptors for Improved Open-Circuit Voltage in Organic Solar Cells.
Jeong, Eunjeong; Takahashi, Kohtaro; Rajagopal, Shinaj K.; Koganezawa, Tomoyuki; Hayashi, Hironobu; Aratani, Naoki; Suzuki, Mitsuharu; Nguyen, Thuc-Quyen; Yamada, Hiroko; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02386

data_4037593
_publ_section_title
;
 Orbital-Energy Modulation of Tetrabenzoporphyrin-Derived Non-Fullerene
 Acceptors for Improved Open-Circuit Voltage in Organic Solar Cells.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02386
_journal_year                    2019
_chemical_formula_moiety         'C38 H20 F6 N4'
_chemical_formula_sum            'C38 H20 F6 N4'
_chemical_formula_weight         646.59
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.708(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   5.02838(14)
_cell_length_b                   15.2818(5)
_cell_length_c                   17.3664(6)
_cell_measurement_reflns_used    12541
_cell_measurement_temperature    103
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      3.56
_cell_volume                     1322.42(8)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17975
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.335
_diffrn_reflns_theta_min         3.566
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             660.00
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0363P)^2^+0.9402P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1931
_reflns_number_total             2400
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo9b02386_si_002.cif
_cod_data_source_block           2CF3BP
_cod_database_code               4037593
_shelx_res_checksum              46914
_shelx_hkl_checksum              18434