Synthesis of π-Conjugated Polymers Containing Organoboron Benzo[h]quinolate in the Main Chain

A study was conducted to synthesize π-conjugated polymers containing organoboron benzo[h]quinolate in the main chain. cTetrahydrofuran (THF) and triethylamine (Et3N) were purified using a two-column solid-state purification system. 10-Hydroxybenzo[h]quinoline, 1,4-diethynyl-2,5- dihexadecyloxybenzene, and 1,4-diethynyl-2-perfluorooctyl-5- trifluoromethylbenzene were prepared to conduct the investigations. Triphenylborane and 10-hydroxybenzo[h]quinoline were dissolved in toluene. The mixture was allowed to stand for 1 day at -20 °C to precipitate a product after the reaction mixture was refluxed for 12 hours. 9.4 mL of n-BuLi was slowly added to the solution of 1,4-diiodobenzene in 75 mL of THF at -78 °C and the mixture was stirred at -78 °C for 1 hour. BBr3 was also added to the reaction mixture at -78 °C and allowed to warm to room temperature and refluxed for 12 hours.