The general procedure for the synthesis of 2,7-dioctylbenzo[b]benzo[4,5]thieno[2,3-d]thiophene from the compound (CAS:1003601-92-0) is as follows: the compound of formula (5) obtained in synthetic Example 1 (300 mg, 0.66 mmol) was added to anhydrous toluene (10 mL) with Pd/C (70 mg). The reaction mixture was depressurized and purged with hydrogen using an aspirator, and this operation was repeated several times. Subsequently, the reaction mixture was stirred for 8 hours. After completion of the reaction, the solvent was removed by distillation. The product was purified by column chromatography (silica gel, hexane, Rf = 0.6) to give 286 mg of product in 94% yield. Further recrystallization from hexane gave a colorless powdery solid (250 mg, 82% yield) as shown in formula (6). This compound corresponds to compound 16 in Table 1. The characterization data were as follows: 1H-NMR (400 MHz, CDCl3): δ 7.75 (d, J = 8.2 Hz, 2H), 7.68 (d, J = 1.5 Hz, 2H), 7.26 (dd, J = 8.2, 1.5 Hz, 2H), 2.74 (t, J = 7.7 Hz, 4H). 1.69 (q, 4H), 1.27-1.34 (m, 20H), 0.88 (t, J = 6.7 Hz, 6H); 13C-NMR (400 MHz, CDCl3): 142.4, 140.0, 132.5, 131.1, 125.8, 123.3, 121.0, 36.1, 31.9, 31.7, 29.5 , 29.33, 29.27, 22.68, 14.1; MS (70 eV, DI) m/z = 464 (M+); melting point 112-113 °C; elemental analysis (C30H40S2) calculated values: C, 77.53; H, 8.67; measured values: C, 77.39; H, 8.67.
![[1]Benzothieno[3,2-b][1]benzothiophene, 2,7-di-1-octyn-1-yl-](/CAS/20210111/GIF/1003601-92-0.gif)
