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_4037591
_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         'C52 H26 F6 N6, C H Cl3'
_chemical_formula_sum            'C53 H27 Cl3 F6 N6'
_chemical_formula_weight         968.15
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.409(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.242(3)
_cell_length_b                   8.6494(13)
_cell_length_c                   30.796(5)
_cell_measurement_reflns_used    1950
_cell_measurement_temperature    90
_cell_measurement_theta_max      20.49
_cell_measurement_theta_min      2.65
_cell_volume                     4325.0(12)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0936
_diffrn_reflns_av_unetI/netI     0.1146
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25145
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         1.432
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       prism
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         8832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.0559
_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^)+(0.0575P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1375
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4847
_reflns_number_total             8832
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02386_si_006.cif
_cod_data_source_block           pCNBP
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4037591
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              85627
_shelx_hkl_checksum              75392