A cathode interlayer based on an indandione-terminated quinoidal compound enables 19% efficiency in binary organic solar cells.
Gu, Haoran; Tong, Yao; Xu, Hongli; Wang, Cheng; Xu, Bowei; Geng, Dongling; Bu, Laju; Ye, Long; Deng, Yunfeng; Geng, Yanhou; Materials horizons 12 (2025) 5380–5387; doi:10.1039/d5mh00536a

data_1574551
_publ_section_title
;
 A cathode interlayer based on an indandione-terminated quinoidal compound
 enables 19% efficiency in binary organic solar cells.
;
_journal_issue                   14
_journal_name_full               'Materials horizons'
_journal_page_first              5380
_journal_page_last               5387
_journal_paper_doi               10.1039/d5mh00536a
_journal_volume                  12
_journal_year                    2025
_chemical_formula_moiety         'C47 H54 O10 P2 S2'
_chemical_formula_sum            'C47 H54 O10 P2 S2'
_chemical_formula_weight         904.96
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-21
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-22 deposited with the CCDC.	2025-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                112.731(13)
_cell_angle_beta                 90.393(9)
_cell_angle_gamma                102.666(10)
_cell_formula_units_Z            4
_cell_length_a                   10.742(3)
_cell_length_b                   19.392(6)
_cell_length_c                   24.568(5)
_cell_measurement_reflns_used    9563
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.699
_cell_measurement_theta_min      3.689
_cell_volume                     4581(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1349
_diffrn_reflns_av_unetI/netI     0.1112
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            71371
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.877
_diffrn_reflns_theta_min         3.246
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.428
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1679 before and 0.1106 after correction.
The Ratio of minimum to maximum transmission is 0.7338.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.168
_refine_diff_density_min         -0.937
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       0.0035(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1127
_refine_ls_number_reflns         17131
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.2306
_refine_ls_R_factor_gt           0.1640
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+50.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3380
_refine_ls_wR_factor_ref         0.3736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9593
_reflns_number_total             17131
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5mh00536a2.cif
_cod_data_source_block           240821dyf_po
_cod_depositor_comments          'Adding full bibliography for 1574551.cif.'
_cod_database_code               1574551
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.793
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C39A-C38A = C40A-C39A = C41A-C40A = C42A-C41A = C43A-C42A = C32A-C31A = C33A-
 C32A
 1.53 with sigma of 0.01
 C39A-C40A \\sim C39A-C40B
 with sigma of 0.02
 C40A-C41A \\sim C40B-C41B
 with sigma of 0.02
 C41A-C42A \\sim C41B-C42A
 with sigma of 0.02
 C39A-C41A \\sim C39A-C41B
 with sigma of 0.04
 C40A-C42A \\sim C40B-C42A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C39A \\sim C40A \\sim C41B \\sim C41A \\sim C40B \\sim C42A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C46A \\sim C47A \\sim O10A \\sim P2A: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
Uanis(O10A) \\sim Ueq, Uanis(C46A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(H39C)=Sof(H39D)=Sof(H42C)=Sof(H42D)=Sof(C40B)=Sof(H40C)=Sof(H40D)=
 Sof(C41B)=Sof(H41C)=Sof(H41D)=1-FVAR(1)
 Sof(H39A)=Sof(H39B)=Sof(C40A)=Sof(H40A)=Sof(H40B)=Sof(C41A)=Sof(H41A)=
 Sof(H41B)=Sof(H42A)=Sof(H42B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C28(H28C,H28D), C29(H29C,H29D), C30(H30C,H30D), C31(H31C,H31D), C32(H32C,
 H32D), C33(H33C,H33D), C34(H34C,H34D), C36(H36C,H36D), C38(H38C,H38D),
 C39(H39E,H39F), C40(H40E,H40F), C41(H41E,H41F), C42(H42E,H42F), C43(H43C,H43D),
  C44(H44C,H44D), C46(H46C,H46D), C28A(H28A,H28B), C29A(H29A,H29B), C30A(H30A,
 H30B), C31A(H31A,H31B), C32A(H32A,H32B), C33A(H33A,H33B), C34A(H34A,H34B),
 C36A(H36A,H36B), C38A(H38A,H38B), C39A(H39A,H39B), C39A(H39C,H39D), C40A(H40A,
 H40B), C41A(H41A,H41B), C42A(H42A,H42B), C42A(H42C,H42D), C43A(H43A,H43B),
 C44A(H44A,H44B), C46A(H46A,H46B), C40B(H40C,H40D), C41B(H41C,H41D)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C17(H17), C22(H22), C23(H23),
 C24(H24), C25(H25), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C11A(H11A),
 C17A(H17A), C22A(H22A), C23A(H23A), C24A(H24A), C25A(H25A)
5.c Idealised Me refined as rotating group:
 C35(H35D,H35E,H35F), C37(H37D,H37E,H37F), C45(H45D,H45E,H45F), C47(H47D,H47E,
 H47F), C35A(H35A,H35B,H35C), C37A(H37A,H37B,H37C), C45A(H45A,H45B,H45C),
 C47A(H47A,H47B,H47C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              96711
_shelx_fab_checksum              20947
_olex2_submission_special_instructions 'No special instructions were received'