Significant decrease in the ionization energy of dinaphtho[2,3-<i>b</i>:2',3'-<i>f</i>]thieno[3,2-<i>b</i>]thiophene (DNTT) solid induced by a pinacolborane group.
Takimiya, Kazuo; Usui, Sayaka; Hanaki, Ryota; Bulgarevich, Kirill; Kawabata, Kohsuke; Nakano, Kyohei; Tajima, Keisuke; Materials horizons 13 (2026) 3117–3126; doi:10.1039/d5mh01969a

data_1577028
_publ_section_title
;
 Significant decrease in the ionization energy of
 dinaphtho[2,3-<i>b</i>:2',3'-<i>f</i>]thieno[3,2-<i>b</i>]thiophene
 (DNTT) solid induced by a pinacolborane group.
;
_journal_issue                   6
_journal_name_full               'Materials horizons'
_journal_page_first              3117
_journal_page_last               3126
_journal_paper_doi               10.1039/d5mh01969a
_journal_volume                  13
_journal_year                    2026
_chemical_formula_moiety         'C24 H21 B O2 S2'
_chemical_formula_sum            'C24 H21 B O2 S2'
_chemical_formula_weight         416.34
_chemical_name_systematic        Bpin-BNTT
_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_date             2020-08-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2026-01-03 deposited with the CCDC.	2026-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.2348(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.4468(4)
_cell_length_b                   8.26896(13)
_cell_length_c                   11.32561(16)
_cell_measurement_reflns_used    10007
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.3280
_cell_measurement_theta_min      1.9540
_cell_volume                     2098.82(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -17.00  29.00   0.50    1.28    --  -46.75  19.00  60.00   92
  2  \w    -42.00 -15.00   0.50    1.28    --  -46.75 110.00 136.00   54
  3  \w    -40.00  27.00   0.50    1.28    --  -46.75  37.00 -90.00  134
  4  \w    -27.00   9.00   0.50    1.28    --   46.75 -19.00-180.00   72
  5  \w     33.00  64.00   0.50    5.12    --  103.81 -57.00-180.00   62
  6  \w     36.00  62.00   0.50    5.12    --  103.81 -57.00-150.00   52
  7  \w     78.00 104.00   0.50    5.12    --  103.81 -99.00 -90.00   52
  8  \w     47.00  99.00   0.50    5.12    --  103.81-110.00  41.00  104
  9  \w     63.00  94.00   0.50    5.12    --  103.81 -99.00  90.00   62
 10  \w     32.00  60.00   0.50    5.12    --  103.81 -57.00  60.00   56
 11  \w     35.00  62.00   0.50    5.12    --  103.81 -57.00  90.00   54
 12  \w     31.00  56.00   0.50    5.12    --  103.81 -57.00  30.00   50
 13  \w     23.00  48.00   0.50    1.28    --   46.75-110.00  41.00   50
 14  \w     31.00  64.00   0.50    5.12    --  103.81 -57.00 120.00   66
 15  \w    -26.00  11.00   0.50    1.28    --   46.75 -19.00 120.00   74
 16  \w    -26.00  11.00   0.50    1.28    --   46.75 -19.00  30.00   74
 17  \w     85.00 145.00   0.50    5.12    --  103.81 110.00 136.00  120
 18  \w     97.00 164.00   0.50    5.12    --  103.81  57.00 -60.00  134
 19  \w    -58.00 -30.00   0.50    5.12    -- -100.00  57.00-120.00   56
 20  \w    -69.00 -27.00   0.50    5.12    -- -100.00  57.00 -60.00   84
 21  \w    -68.00 -29.00   0.50    5.12    -- -100.00  57.00 -30.00   78
 22  \w    -61.00 -34.00   0.50    5.12    -- -100.00  57.00   0.00   54
 23  \w    -70.00 -36.00   0.50    5.12    -- -100.00  57.00  90.00   68
 24  \w    -68.00 -28.00   0.50    5.12    -- -100.00  57.00 120.00   80
 25  \w    -86.00 -46.00   0.50    1.28    --  -46.75 110.00 136.00   80
 26  \w   -107.00 -31.00   0.50    5.12    -- -100.00 110.00 136.00  152
 27  \w   -156.00-131.00   0.50    5.12    -- -100.00-110.00  41.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0613459000
_diffrn_orient_matrix_UB_12      0.0023960000
_diffrn_orient_matrix_UB_13      0.0680817000
_diffrn_orient_matrix_UB_21      -0.0074100000
_diffrn_orient_matrix_UB_22      0.1819706000
_diffrn_orient_matrix_UB_23      0.0244418000
_diffrn_orient_matrix_UB_31      -0.0300859000
_diffrn_orient_matrix_UB_32      -0.0399138000
_diffrn_orient_matrix_UB_33      0.1154721000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14955
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.639
_diffrn_reflns_theta_min         1.971
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.432
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.74a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0578P)^2^+0.3699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3821
_reflns_number_total             4195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5mh01969a2.cif
_cod_data_source_block           200803_usui_bpinbntt
_cod_database_code               1577028
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C39 H39 B39 S39 O1 '
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.443
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C5(H5), C10(H10), C7(H7), C8(H8), C15(H15), C18(H18), C16(H16),
 C17(H17)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_shelx_res_checksum              96397
_olex2_exptl_crystal_mounting_method 'Capton loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.345
_oxdiff_exptl_absorpt_empirical_full_min 0.646