90007015

open access

Accepted Manuscript

Thermally Induced Self-Doping of π-Conjugated Polymers Bearing a Pendant Neopentyl Sulfonate Group

Macromolecules

53(46)

1171-1179

American Chemical Society

2020-02-25

2021-03-01

Published online 12 February 2020

A regioregular head-to-tail (HT)-type polythiophene was synthesized by the deprotonative nickel-catalyzed cross-coupling polymerization of 2-chlorothiophene bearing a neopentyl benzenesulfonate group at the 3-position. The obtained HT-regioregular polymer was found to dissolve in chloroform or THF, while it became soluble in water upon heating at 185 °C for 10 min by the liberation of the protected neopentyl group. The thin film of the polymer showed a remarkable improvement in conductivity of ca. 10(3) times before/after heating, suggesting the thermally induced intramolecular doping of polythiophene by the formed sulfonic acid at the side chain. The related doping was also observed in a poly(phenylacetylene) derivative, which was synthesized by rhodium-catalyzed polymerization. Copolymerization of such thiophene- and acetylene-bearing neopentyl sulfonate with 3-alkylthiophene and phenylacetylene, respectively, produced the corresponding statistical copolymers, demonstrating the formal self-doping of poly(3-alkylthiophene) and poly(phenylacetylene).

polyacetylene

学術雑誌論文

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Macromolecules, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.macromol.9b02554