ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

A new synthetic route for the production of a thiophene-based methine-bridged type conjugated polymer

Mai Ichikawa and Hiromasa Goto

Department of Materials Science, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Japan

E-mail: gotoh@ims.tsukuba.ac.jp

Received: 29 November 2020  Accepted: 22 January 2021

Abstract:

Methine-bridged type π-conjugated polymer was synthesized using a Migita–Kosugi–Stille polycondensation reaction in the presence of a Pd(0) catalyst followed by oxidation with 2,3-dichloro-5,6-dicyano-p-benzoquinone. The chemical structure of the obtained polymer was confirmed by infrared absorption spectroscopy. The optical properties of the polymer were confirmed by ultraviolet visible optical absorption and photoluminescence spectra. Vapor phase iodine doping was performed to generate a charge carrier in the polymer. The magnetic properties of the carrier were examined by electron spin resonance (ESR). The doped polymer exhibited Pauli’s para-magnetism with constant ESR linewidths and g-values, whereas the ESR intensity increased with decrease in temperature. This indicated the formation of charge carriers on the backbone of the polymer by iodine doping, which is typical behavior of polarons in conductive polymers. The present study describes the first synthesis of a methane-bridged π-conjugated polymer using a Migita–Kosugi–Stille type polycondensation.

Graphical abstract

Keywords: Conjugated polymer; Methine bridge; Pauli’s para-magnetism; Polarons; Polycondensation

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01536-8

Chemical Papers 75 (10) 5133–5138 (2021)