Synthesis of 2,7-dioctylbiphenylenodithiophenes for use as organic semiconducting materials in solution-processed organic thin-film transistors
Watanabe, Makoto; Miyashita, Masato; Fukuda, Takashi; Oku, Shinya; CrystEngComm  (2026) –; doi:10.1039/D5CE01050K

data_7251778
_publ_section_title
;
 Synthesis of 2,7-dioctylbiphenylenodithiophenes for use as organic
 semiconducting materials in solution-processed organic thin-film
 transistors
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              2234
_journal_page_last               2242
_journal_paper_doi               10.1039/D5CE01050K
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C32 H40 S2'
_chemical_formula_sum            'C32 H40 S2'
_chemical_formula_weight         488.76
_chemical_melting_point          381
_chemical_name_systematic        2,7-dioctylbiphenyleno[1,2-b:5,6-b']dithiophene
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-14
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-07-31 deposited with the CCDC.	2026-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                116.814(2)
_cell_angle_beta                 95.590(2)
_cell_angle_gamma                92.275(2)
_cell_formula_units_Z            1
_cell_length_a                   5.72410(10)
_cell_length_b                   11.0388(2)
_cell_length_c                   11.8971(3)
_cell_measurement_reflns_used    6070
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.2280
_cell_measurement_theta_min      4.2070
_cell_volume                     664.76(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_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 0.993
_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     20.00  83.00   0.50    0.05    --    0.00  77.00-180.00  126
  2  \w    -45.00  10.00   0.50    0.05    --    0.00  77.00-180.00  110
  3  \w   -102.00 -74.00   0.50    0.05    --    0.00   0.00-120.00   56
  4  \w    -99.00 -74.00   0.50    0.05    --    0.00   0.00-180.00   50
  5  \w   -102.00 -77.00   0.50    0.05    --    0.00   0.00-150.00   50
  6  \w   -102.00 -77.00   0.50    0.05    --    0.00   0.00 -90.00   50
  7  \w   -100.00 -75.00   0.50    0.05    --    0.00   0.00 -60.00   50
  8  \w    -99.00 -74.00   0.50    0.05    --    0.00   0.00  60.00   50
  9  \w    -75.00 -23.00   0.50    0.05    --    0.00 139.00  -8.00  104
 10  \w    -46.00 -20.00   0.50    0.05    --   18.00 128.00 -83.83   52
 11  \w    -61.00 -34.00   0.50    0.05    --    0.00 130.00 177.00   54
 12  \w   -148.00-117.00   0.50    0.05    -- -106.00   0.00 -60.00   62
 13  \w    -52.00 -27.00   0.50    0.05    -- -106.00  63.00-150.00   50
 14  \w    -14.00  22.00   0.50    0.05    --  -57.73  15.00 -60.00   72
 15  \w    -11.00  15.00   0.50    0.05    --  -57.73  15.00 -30.00   52
 16  \w     13.00  39.00   0.50    0.05    --   62.00  84.00  -2.85   52
 17  \w     93.00 134.00   0.50    0.05    --   57.73 139.00  -8.00   82
 18  \w    100.00 131.00   0.50    0.05    --  115.46 139.00  -8.00   62
 19  \w     63.00  88.00   0.50    0.05    --  115.46 178.00 120.00   50
 20  \w    107.00 132.00   0.50    0.05    --  115.46 178.00 120.00   50
 21  \w    120.00 145.00   0.50    0.05    --  115.46 130.00 177.00   50
 22  \w      5.00  31.00   0.50    0.05    --   62.00  95.00 118.56   52
 23  \w     14.00  40.00   0.50    0.05    --   66.00  92.00  82.53   52
 24  \w      0.00  25.00   0.50    0.05    --   57.73  98.00  60.81   50
 25  \w      3.00  35.00   0.50    0.05    --   57.73  91.00 134.23   64
 26  \w      6.00  31.00   0.50    0.05    --   62.00  93.00  36.17   50
 27  \w      5.00  30.00   0.50    0.05    --   62.00  94.00 -71.96   50
 28  \w     14.00  39.00   0.50    0.05    --   70.00  92.00-131.79   50
 29  \w      4.00  29.00   0.50    0.05    --   57.73  89.00-105.99   50
 30  \w     13.00  41.00   0.50    0.05    --   66.00  87.00 -46.08   56
 31  \w     16.00  42.00   0.50    0.05    --   66.00  89.00 172.57   52
 32  \w     83.00 173.00   0.50    0.05    --  115.46  77.00  90.00  180
 33  \w    153.00 178.00   0.50    0.05    --  115.46  77.00 150.00   50
 34  \w    148.00 173.00   0.50    0.05    --  115.46  77.00 120.00   50
 35  \w     81.00 147.00   0.50    0.05    --  115.46  77.00 150.00  132
 36  \w     69.00  95.00   0.50    0.05    --  115.46  77.00 120.00   52
 37  \w    112.00 137.00   0.50    0.05    --  115.46  77.00 120.00   50
 38  \w     69.00 144.00   0.50    0.05    --  115.46  77.00  60.00  150
 39  \w     27.00  88.00   0.50    0.05    --   74.00  75.00  42.92  122
 40  \w     94.00 120.00   0.50    0.05    --   74.00  75.00  42.92   52
 41  \w     68.00 164.00   0.50    0.05    --  115.46  77.00 -30.00  192
 42  \w     29.00  55.00   0.50    0.05    --   74.00  74.00 -60.51   52
 43  \w     79.00 164.00   0.50    0.05    --  115.46  63.00-150.00  170
 44  \w    120.00 155.00   0.50    0.05    --   74.00  74.00 -60.51   70
 45  \w    107.00 139.00   0.50    0.05    --   57.73   0.00-120.00   64
 46  \w    109.00 139.00   0.50    0.05    --   57.73   0.00-180.00   60
 47  \w    110.00 139.00   0.50    0.05    --   57.73   0.00-150.00   58
 48  \w    108.00 137.00   0.50    0.05    --   57.73   0.00 -90.00   58
 49  \w    108.00 140.00   0.50    0.05    --   57.73   0.00 -60.00   64
 50  \w    109.00 135.00   0.50    0.05    --   57.73   0.00 -30.00   52
 51  \w    110.00 177.00   0.50    0.05    --  115.46   0.00 -90.00  134
 52  \w     77.00 108.00   0.50    0.05    --  115.46  63.00 -90.00   62
 53  \w     78.00 153.00   0.50    0.05    --  115.46  63.00 -60.00  150
 54  \w     69.00 156.00   0.50    0.05    --  115.46  37.00  60.00  174
 55  \w    111.00 140.00   0.50    0.05    --   57.73   0.00 150.00   58
 56  \w     31.00  76.00   0.50    0.05    --  115.46 -63.00 150.00   90
 57  \w     43.00  74.00   0.50    0.05    --  115.46 -63.00 120.00   62
 58  \w     31.00  58.00   0.50    0.05    --  115.46 -50.00  60.00   54
 59  \w    -36.00  17.00   0.50    0.05    --   57.73 -15.00 150.00  106
 60  \w    -39.00  14.00   0.50    0.05    --   57.73 -15.00 -90.00  106
 61  \w     18.00  73.00   0.50    0.05    --  115.46 -91.00 -90.00  110
 62  \w     84.00 110.00   0.50    0.05    --  115.46-139.00 -68.00   52
 63  \w     72.00  97.00   0.50    0.05    --   57.73-139.00 -68.00   50
 64  \w     41.00 105.00   0.50    0.05    --  115.46-111.00  90.00  128
 65  \w     66.00  92.00   0.50    0.05    --  115.46-130.00 105.00   52
 66  \w     35.00  66.00   0.50    0.05    --  115.46-111.00 150.00   62
 67  \w     77.00 107.00   0.50    0.05    --  115.46-111.00 150.00   60
 68  \w     54.00 113.00   0.50    0.05    --   57.73-130.00 105.00  118
 69  \w     30.00  65.00   0.50    0.05    --  115.46 -91.00 -60.00   70
 70  \w     79.00 106.00   0.50    0.05    --  115.46 -91.00 -60.00   54
 71  \w     79.00 104.00   0.50    0.05    --  115.46 -91.00 -90.00   50
 72  \w    -96.00 -65.00   0.50    0.05    --  -57.73 139.00  -8.00   62
 73  \w    -77.00 -47.00   0.50    0.05    -- -106.00 111.00 -60.00   60
 74  \w    -77.00 -52.00   0.50    0.05    --  -57.73 130.00 177.00   50
 75  \w    -83.00 -56.00   0.50    0.05    -- -106.00 130.00 177.00   54
 76  \w    -79.00 -53.00   0.50    0.05    --  -94.00 -66.00 -93.88   52
 77  \w    -82.00 -56.00   0.50    0.05    -- -102.00 -77.00 -17.01   52
 78  \w    -68.00 -42.00   0.50    0.05    --  -90.00 -77.00   7.85   52
 79  \w    -78.00 -51.00   0.50    0.05    --  -98.00 -77.00   1.94   54
 80  \w    -88.00 -58.00   0.50    0.05    -- -106.00 -77.00 -30.00   60
 81  \w    -84.00 -58.00   0.50    0.05    -- -106.00 -77.00-150.00   52
 82  \w   -177.00-130.00   0.50    0.05    -- -106.00 -77.00 -30.00   94
 83  \w   -174.00-134.00   0.50    0.05    --  -90.00 -77.00   7.85   80
 84  \w   -104.00 -58.00   0.50    0.05    -- -106.00 -77.00 150.00   92
 85  \w    -94.00 -58.00   0.50    0.05    -- -106.00 -77.00  60.00   72
 86  \w   -177.00-134.00   0.50    0.05    -- -102.00 -77.00 -17.01   86
 87  \w   -100.00 -58.00   0.50    0.05    -- -106.00 -77.00 -60.00   84
 88  \w    -84.00 -58.00   0.50    0.05    -- -106.00 -77.00 -90.00   52
 89  \w    -83.00 -58.00   0.50    0.05    -- -106.00 -77.00-120.00   50
 90  \w    -86.00 -58.00   0.50    0.05    -- -106.00 -77.00-180.00   56
 91  \w   -128.00-102.00   0.50    0.05    -- -106.00 -77.00-180.00   52
 92  \w   -156.00-130.00   0.50    0.05    -- -106.00 -77.00-180.00   52
 93  \w   -169.00-112.00   0.50    0.05    --  -74.00 -76.00 -94.07  114
 94  \w   -158.00-120.00   0.50    0.05    -- -106.00 -77.00-120.00   76
 95  \w    -73.00 -47.00   0.50    0.05    --  -94.00 -76.00-117.08   52
 96  \w    -52.00 -27.00   0.50    0.05    --  -74.00 -76.00 -94.07   50
 97  \w    -80.00 -55.00   0.50    0.05    -- -102.00 -76.00  -5.85   50
 98  \w   -174.00-149.00   0.50    0.05    --  -94.00 -76.00-117.08   50
 99  \w   -146.00 -59.00   0.50    0.05    -- -106.00 -77.00  30.00  174
100  \w   -130.00 -63.00   0.50    0.05    -- -106.00 -74.00  42.78  134
101  \w   -165.00-139.00   0.50    0.05    -- -106.00 -73.00  63.88   52
102  \w   -177.00-122.00   0.50    0.05    -- -106.00 -75.00 145.62  110
103  \w   -112.00 -66.00   0.50    0.05    -- -106.00 -75.00 145.62   92
104  \w    -80.00 -55.00   0.50    0.05    -- -102.00 -76.00 107.70   50
105  \w    -87.00 -61.00   0.50    0.05    -- -106.00 -72.00  77.05   52
106  \w    -87.00 -60.00   0.50    0.05    -- -106.00 -73.00  63.88   54
107  \w    -74.00 -49.00   0.50    0.05    --  -94.00 -72.00  69.08   50
108  \w    -59.00 -29.00   0.50    0.05    --  -74.00 -72.00  79.20   60
109  \w    -78.00 -53.00   0.50    0.05    --  -98.00 -71.00  58.10   50
110  \w    -82.00 -48.00   0.50    0.05    --  -94.00 -73.00  48.43   68
111  \w    -92.00 -61.00   0.50    0.05    -- -106.00 -70.00 101.43   62
112  \w   -164.00-138.00   0.50    0.05    --  -74.00 -72.00  79.20   52
113  \w    -61.00 -35.00   0.50    0.05    --  -78.00 -69.00 125.61   52
114  \w    -62.00 -37.00   0.50    0.05    --  -82.00 -70.00-121.56   50
115  \w    -64.00 -39.00   0.50    0.05    --  -82.00 -67.00 -76.90   50
116  \w    -68.00 -38.00   0.50    0.05    --  -82.00 -69.00-172.55   60
117  \w   -101.00 -63.00   0.50    0.05    -- -106.00 -66.00-150.59   76
118  \w   -101.00 -66.00   0.50    0.05    -- -106.00 -72.00-165.52   70
119  \w   -174.00-107.00   0.50    0.05    -- -106.00 -72.00-165.52  134
120  \w   -172.00-146.00   0.50    0.05    --  -82.00 -69.00-172.55   52
121  \w    -70.00 -44.00   0.50    0.05    --  -86.00 -66.00 167.18   52
122  \w   -169.00-127.00   0.50    0.05    --  -86.00 -66.00 167.18   84
123  \w   -117.00 -82.00   0.50    0.05    -- -106.00-130.00 105.00   70
124  \w   -121.00 -71.00   0.50    0.05    --  -57.73-130.00 105.00  100
125  \w   -128.00-103.00   0.50    0.05    --  -57.73-139.00 -68.00   50
126  \w   -119.00 -93.00   0.50    0.05    -- -106.00-139.00 -68.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0402542000
_diffrn_orient_matrix_UB_12      -0.1430753000
_diffrn_orient_matrix_UB_13      -0.1145844000
_diffrn_orient_matrix_UB_21      -0.0094949000
_diffrn_orient_matrix_UB_22      -0.0642181000
_diffrn_orient_matrix_UB_23      0.0908486000
_diffrn_orient_matrix_UB_31      -0.2684623000
_diffrn_orient_matrix_UB_32      0.0087583000
_diffrn_orient_matrix_UB_33      -0.0051774000
_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  0.0462
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10389
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.484
_diffrn_reflns_theta_max         67.484
_diffrn_reflns_theta_min         4.199
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.932
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       needle
_exptl_crystal_F_000             264
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: heptane'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0008(5)
_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   1.028
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0550P)^2^+0.1768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2288
_reflns_number_total             2380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce01050k2.cif
_cod_data_source_block           mm1304
_cod_depositor_comments
'Adding full bibliography for 7251778--7251779.cif.'
_cod_database_code               7251778
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C32 H40 S2'
_shelx_estimated_absorpt_t_max   0.830
_shelx_estimated_absorpt_t_min   0.595
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   285
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.967
_oxdiff_exptl_absorpt_empirical_full_min 0.424