Regulating the reorganization energy and crystal packing of small-molecule donors enables the high performance of binary all-small-molecule organic solar cells with a slow film growth rate
Xu, Tongle; Lv, Jie; Zheng, Daming; Luo, Zhenghui; Jee, Min Hun; Ran, Guangliu; Chen, Zhanxiang; Huang, Zhongyan; Ren, Jiaqi; Li, Yuxiang; Zhang, Cai’e; Hu, Hanlin; Pauporté, Thierry; Zhang, Wenkai; Woo, Han Young; Yang, Chuluo; Energy & Environmental Science 16 (2023) 5933–5943; doi:10.1039/D3EE02129G

data_1570150
_publ_section_title
;
 Regulating the reorganization energy and crystal packing of
 small-molecule donors enables the high performance of binary
 all-small-molecule organic solar cells with a slow film growth rate
;
_journal_issue                   12
_journal_name_full               'Energy &amp; Environmental Science'
_journal_page_first              5933
_journal_page_last               5943
_journal_paper_doi               10.1039/D3EE02129G
_journal_volume                  16
_journal_year                    2023
_chemical_formula_moiety         'C108 H138 F2 N2 O2 S12 Si2, 2(C4 H8 O)'
_chemical_formula_sum            'C116 H154 F2 N2 O4 S12 Si2'
_chemical_formula_weight         2119.30
_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             2023-09-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-20 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                82.2010(10)
_cell_angle_beta                 85.7120(10)
_cell_angle_gamma                75.2340(10)
_cell_formula_units_Z            1
_cell_length_a                   12.5553(4)
_cell_length_b                   14.6952(4)
_cell_length_c                   16.3320(5)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.43
_cell_volume                     2884.29(15)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_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            65141
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.109
_diffrn_reflns_theta_min         2.141
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1075 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.9398.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             1134
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     753
_refine_ls_number_reflns         12677
_refine_ls_number_restraints     373
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0771P)^2^+1.7431P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10211
_reflns_number_total             12677
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ee02129g2.cif
_cod_data_source_block           mo_220819_t26_0m
_cod_depositor_comments
'Adding full bibliography for 1570150--1570151.cif.'
_cod_database_code               1570150
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.910
_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
 C9-C10
 1.53 with sigma of 0.01
 C10A-C11A
 1.53 with sigma of 0.01
 C10-C11
 1.53 with sigma of 0.01
 C38-C40 \\sim C38A-C40A
 with sigma of 0.04
 C39-C40 \\sim C39A-C40A
 with sigma of 0.02
 Si1-C9 \\sim Si1-C9A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 C11-C10 \\sim C11A-C10A
 with sigma of 0.02
 Si1-C10 \\sim Si1-C10A
 with sigma of 0.04
 C9-C11 \\sim C9A-C11A
 with sigma of 0.04
 Si1-C15 \\sim Si1-C15A
 with sigma of 0.02
 C15-C16 \\sim C15A-C16A
 with sigma of 0.02
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 Si1-C16 \\sim Si1-C16A
 with sigma of 0.04
 C15-C17 \\sim C15A-C17A
 with sigma of 0.04
 C52-C53 \\sim C52-C53A
 with sigma of 0.02
 C53-C54 \\sim C53A-C54A
 with sigma of 0.02
 C52-C54 \\sim C52-C54A
 with sigma of 0.04
 C37-C38 \\sim C37A-C38A
 with sigma of 0.02
 C37-C39 \\sim C37A-C39A
 with sigma of 0.04
 C35-C36 \\sim C35-C36A
 with sigma of 0.02
 C36-C37 \\sim C36A-C37A
 with sigma of 0.02
 C38-C39 \\sim C38A-C39A
 with sigma of 0.02
 C35-C37 \\sim C35-C37A
 with sigma of 0.04
 C36-C38 \\sim C36A-C38A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C33 \\sim C35 \\sim C36 \\sim C36A \\sim C37 \\sim C37A \\sim C38 \\sim C38A
\\sim C39 \\sim C39A \\sim C40A \\sim C40: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.02 within 2A
Si1 \\sim C9 \\sim C10 \\sim C11 \\sim C9A \\sim C10A \\sim C11A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Si1 \\sim C15 \\sim C16 \\sim C17 \\sim C15A \\sim C16A \\sim C17A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C52 \\sim C53 \\sim C54 \\sim C53A \\sim C54A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(C11A)=
 Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=
 Sof(H11B)=Sof(H11C)=FVAR(1)
 Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(C17A)=
 Sof(H17D)=Sof(H17E)=Sof(H17F)=1-FVAR(2)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=
 Sof(H17B)=Sof(H17C)=FVAR(2)
 Sof(H52C)=Sof(H52D)=Sof(C53A)=Sof(H53C)=Sof(H53D)=Sof(C54A)=Sof(H54D)=
 Sof(H54E)=Sof(H54F)=1-FVAR(3)
 Sof(H52A)=Sof(H52B)=Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(C54)=Sof(H54A)=Sof(H54B)=
 Sof(H54C)=FVAR(3)
 Sof(H35C)=Sof(H35D)=Sof(C36A)=Sof(H36C)=Sof(H36D)=Sof(C37A)=Sof(H37C)=
 Sof(H37D)=Sof(C38A)=Sof(H38C)=Sof(H38D)=Sof(C39A)=Sof(H39C)=Sof(H39D)=
 Sof(C40A)=Sof(H40D)=Sof(H40E)=Sof(H40F)=1-FVAR(4)
 Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C37)=Sof(H37A)=Sof(H37B)=
 Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(C40)=Sof(H40A)=
 Sof(H40B)=Sof(H40C)=FVAR(4)
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,
 H27B), C28(H28A,H28B), C29(H29A,H29B), C35(H35A,H35B), C35(H35C,H35D),
 C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C49(H49A,H49B),
  C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B), C52(H52C,H52D), C9(H9A,H9B),
 C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C53(H53A,H53B), C9A(H9AA,H9AB),
  C10A(H10C,H10D), C15A(H15C,H15D), C16A(H16C,H16D), C53A(H53C,H53D), C55(H55A,
 H55B), C56(H56A,H56B), C57(H57A,H57B), C58(H58A,H58B), C36A(H36C,H36D),
 C37A(H37C,H37D), C38A(H38C,H38D), C39A(H39C,H39D)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C19(H19), C22(H22), C32(H32), C42(H42), C43(H43),
 C45(H45)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C30(H30A,H30B,H30C), C40(H40A,H40B,H40C), C11(H11A,H11B,
 H11C), C17(H17A,H17B,H17C), C54(H54A,H54B,H54C), C11A(H11D,H11E,H11F),
 C17A(H17D,H17E,H17F), C54A(H54D,H54E,H54F), C40A(H40D,H40E,H40F)
;
_shelx_res_checksum              62311
_olex2_submission_special_instructions 'No special instructions were received'