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_1577027
_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         'C28 H23 B O2 S2'
_chemical_formula_sum            'C28 H23 B O2 S2'
_chemical_formula_weight         466.39
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-12-31
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-03 deposited with the CCDC.	2026-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.709(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.0771(19)
_cell_length_b                   7.6507(4)
_cell_length_c                   12.2423(5)
_cell_measurement_reflns_used    5139
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8860
_cell_measurement_theta_min      3.4930
_cell_volume                     2343.9(2)
_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 1.5 (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      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.940
_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    -36.00  10.00   0.50   31.33    --   41.05 -19.00 -30.00   92
  2  \w    -32.00  15.00   0.50   31.33    --   41.05 -86.00 -27.00   94
  3  \w    -33.00  13.00   0.50   31.33    --   41.05 -19.00-120.00   92
  4  \w     36.00 137.00   0.50  125.31    --  105.51 -86.00 -27.00  202
  5  \w     78.00 105.00   0.50  125.31    --  105.51 -94.00-180.00   54
  6  \w     81.00 109.00   0.50  125.31    --  105.51-125.00-180.00   56
  7  \w     38.00  68.00   0.50  125.31    --  105.51 -61.00-180.00   60
  8  \w     38.00  64.00   0.50  125.31    --  105.51 -61.00-150.00   52
  9  \w     37.00  68.00   0.50  125.31    --  105.51 -94.00-180.00   62
 10  \w     33.00  71.00   0.50  125.31    --  105.51-125.00-180.00   76
 11  \w     32.00  70.00   0.50  125.31    --  105.51 -61.00 -90.00   76
 12  \w     34.00  70.00   0.50  125.31    --  105.51 -61.00   0.00   72
 13  \w     39.00  70.00   0.50  125.31    --  105.51 -61.00  30.00   62
 14  \w     33.00  71.00   0.50  125.31    --  105.51 -61.00  90.00   76
 15  \w     32.00  65.00   0.50  125.31    --  105.51 -61.00 120.00   66
 16  \w     90.00 127.00   0.50  125.31    --  105.51  30.00  30.00   74
 17  \w    129.00 167.00   0.50  125.31    --  105.51  30.00  30.00   76
 18  \w    126.00 151.00   0.50  125.31    --  105.51  86.00  91.00   50
 19  \w     50.00  80.00   0.50   31.33    --   41.05  57.00 120.00   60
 20  \w    -38.00  12.00   0.50   31.33    --   41.05 -19.00   0.00  100
 21  \w    -74.00  26.00   0.50   31.33    --  -41.05  86.00  91.00  200
 22  \w    -80.00 -55.00   0.50  125.31    -- -100.00  86.00  91.00   50
 23  \w    -51.00 -26.00   0.50  125.31    -- -100.00  45.00  30.00   50
 24  \w    -73.00 -27.00   0.50  125.31    -- -100.00  61.00 -60.00   92
 25  \w    -52.00 -25.00   0.50  125.31    -- -100.00  45.00 -90.00   54
 26  \w    -52.00 -27.00   0.50  125.31    -- -100.00  45.00 -60.00   50
 27  \w    -50.00 -24.00   0.50  125.31    -- -100.00  45.00-150.00   52
 28  \w   -164.00 -84.00   0.50  125.31    -- -100.00 -86.00 -27.00  160
;
_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      -0.0336089000
_diffrn_orient_matrix_UB_12      0.1528790000
_diffrn_orient_matrix_UB_13      -0.0488920000
_diffrn_orient_matrix_UB_21      0.0515379000
_diffrn_orient_matrix_UB_22      0.0941846000
_diffrn_orient_matrix_UB_23      -0.0292455000
_diffrn_orient_matrix_UB_31      -0.0032578000
_diffrn_orient_matrix_UB_32      -0.0909526000
_diffrn_orient_matrix_UB_33      -0.1124349000
_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  0.0803
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13628
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.256
_diffrn_reflns_theta_min         3.532
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47647
_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 yellow'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0762
_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^)+(0.1794P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2166
_refine_ls_wR_factor_ref         0.2493
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3308
_reflns_number_total             4623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5mh01969a2.cif
_cod_data_source_block           exp_112
_cod_database_code               1577027
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C96 H56 O4 S8 B1 '
_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. Rigid body (RIGU) restrains
 C3, C1, C7, C2, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O7, O10, O15, O13, C11, C00S, C13, C6, C8, C2, C5, C00T, C7, C1, C4, C3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: C00S(0.5) C00T(0.5) C11(0.5) C13(0.5) O7(0.5) O10(0.5) O13(0.5)
 O15(0.5) C2(0.5) H2A(0.5) H2B(0.5) H2C(0.5) C5(0.5) H5A(0.5) H5B(0.5) H5C(0.5)
 C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5) C3(0.5)
 H3A(0.5) H3B(0.5) H3C(0.5) C8(0.5) H8A(0.5) H8B(0.5) H8C(0.5) C4(0.5) H4A(0.5)
 H4B(0.5) H4C(0.5) C6(0.5) H6A(0.5) H6B(0.5) H6C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C00B(H00B), C00G(H00G), C00I(H00I), C00J(H00J), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
4.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C5(H5A,H5B,H5C), C1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C3(H3A,
 H3B,H3C), C8(H8A,H8B,H8C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              45227
_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 3.233
_oxdiff_exptl_absorpt_empirical_full_min 0.312