Poly(3-hexylthiophene) (P3HT) is an organic semiconducting polymer that finds widespread use in applications such as organic photovoltaics and in field effect transistors. Prior work from others have produced a synthesis that forms P3HT in high yield and high regioregularity which proceeds through a direct arylation polymerization (DArP) utilizing a palladium catalyst, inorganic base, and phosphine ligand. The focus of this research is to expand on this procedure by investigating alternative ether solvents to replace tetrahydrofuran (THF) and bases to replace CsCO3 in the synthesis of P3HT. The solvents investigated were 2-methyltetrahydrofuran (2-MeTHF), cyclopentylmethylether (CPME), anisole, and THF as a control. The investigated base was K2CO3. The resulting polymers were obtained in yields comparable to the literature and analyzed with several analytical methods including NMR spectroscopy, UV-Vis spectroscopy, and gel-permeation chromatography. It was found that using 2-MeTHF as a solvent and K2CO3 as a base produced a polymer with the highest molecular weight and regioregularity. These results show that utilizing green solvents and simple bases for the DArP synthesis of P3HT is a viable option for producing polymers with desirable properties.

Solvent and base effects in the synthesis of poly(3-hexylthiophene) via direct arylation polymerizations

251st National Meeting (2016)

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