345633-76-3

104934-52-3

345633-76-3

General procedure for the synthesis of 4,4'-didodecyl-2,2'-bithiophene from 3-dodecylthiophene: rt-BuLi (7.04 mL, 2.5 M hexane solution) was slowly added dropwise under stirring to a solution containing 3-dodecylthiophene (4.000 g, 15.8 mmol) and N,N,N',N'-tetramethylethylenediamine (2.75 mL, 17.6 mmol) in solution. Subsequently, 80.0 mL of anhydrous ether was added at -78 °C. The reaction mixture was gradually warmed to room temperature and refluxed for 1 hour. Upon completion of the reaction, the mixture was cooled to -78 °C and CuCl2 (2.640 g, 19.6 mmol) was added all at once. The reaction mixture was stirred overnight, during which the temperature naturally increased to room temperature. At the end of the reaction, the reaction was quenched with water and the mixture was extracted with chloroform. The organic layers were combined, washed with water, dried with MgSO4, filtered and concentrated to dryness. The crude product was purified by silica gel column chromatography using hexane as eluent to give a mixture of 4,4'- and 3,3'-bisdodecylthiophene (about 15% of the target product in the mixture as determined by 1H NMR). Finally, purified 4,4'-bidodecyl-2,2'-bithiophene (25) was obtained as a white solid (2.200 g, 55% yield) by recrystallization from a solvent mixture of acetone:ethanol (1:1).1H NMR (CDCl3) data: δ 0.91 (t, 6H), 1.33 (m, 36H), 1.66 (q, 4H), 2.60 (t , 4H), 6.80 (s, 2H), 7.01 (s, 2H) ppm.