The general procedure for the synthesis of 2-trimethylsilylthienylthiophene from 2-trimethylsilylthienylthiophene was as follows: 2-[(trimethylmethylsilyl)ethynyl]thiophene (1 mmol), an inorganic base (potassium tert-butoxide, sodium tert-butoxide, potassium hydroxide, sodium hydroxide, or potassium trimethylsilyl, sodium trimethylsilyl, 0.05 mmol), and 2 mL of DMA or DMSO solvent were added in turn to a 10-mL in a sealed tube. The reaction mixture was placed in an oil bath at 60 °C and stirred for 6 h, during which the reaction progress was monitored by TLC. Upon completion of the reaction, an equal volume of homotrimethylene or n-undecane was added to the crude product. The exact yield of the product was determined by GC and GC-MS. The yields of the products were 59%, 66%, 75%, 77%, 92%, and 85% when DMSO was used as the reaction solvent and potassium tert-butanol, sodium tert-butanol, potassium hydroxide, sodium hydroxide, or potassium trimethylmethylsilyl, sodium trimethylmethylsilyl were used as the catalysts, respectively. When DMA was used as the reaction solvent, with the same catalyst, the yields of the products were 51%, 60%, 67%, 70%, 81%, 72%, respectively.
