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_4037595
_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         'C60 H42 F6 N6'
_chemical_formula_sum            'C60 H42 F6 N6'
_chemical_formula_weight         960.99
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 116.9630(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.9470(16)
_cell_length_b                   7.9948(7)
_cell_length_c                   17.5113(16)
_cell_measurement_reflns_used    2608
_cell_measurement_temperature    90
_cell_measurement_theta_max      24.66
_cell_measurement_theta_min      2.55
_cell_volume                     2239.5(3)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 '
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0404
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14349
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.564
_diffrn_reflns_theta_min         2.328
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       prism
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0540
_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^)+(0.1000P)^2^+0.3419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1731
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3440
_reflns_number_total             5175
_reflns_threshold_expression     'I > 2\s'
_cod_data_source_file            jo9b02386_si_007.cif
_cod_data_source_block           pCNCP
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037595
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              73359
_shelx_hkl_checksum              7129