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Synthesis and characterization of cyclobutenedione–bithiophene π-conjugated polymers: acetal-protecting strategy for Kumada–Tamao–Corriu coupling polymerization between aryl bromide and Grignard reagents

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Abstract

Cyclobutenedione is an aromatic ring that exhibits strong electron-withdrawing properties but is susceptible to undesired reactions with nucleophiles. Herein, Kumada–Tamao–Corriu coupling polymerization of a cyclobutenedione monomer whose carbonyl groups are protected as acetals was achieved. Hydrolysis of the acetals afforded donor–acceptor type π-conjugated polymers consisting of cyclobutenedione as an acceptor unit and bithiophene as a donor unit. The acetal-protected monomer was also subjected to Suzuki–Miyaura coupling polymerization. The absorption and emission spectra of the deprotected polymers shifted to the longer wavelength compared with the acetal-protected polymers.

Graphical abstract: Synthesis and characterization of cyclobutenedione–bithiophene π-conjugated polymers: acetal-protecting strategy for Kumada–Tamao–Corriu coupling polymerization between aryl bromide and Grignard reagents

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Supplementary files

Article information


Submitted
11 Oct 2019
Accepted
02 Dec 2019
First published
11 Dec 2019

This article is Open Access

RSC Adv., 2019,9, 40863-40872
Article type
Paper

Synthesis and characterization of cyclobutenedione–bithiophene π-conjugated polymers: acetal-protecting strategy for Kumada–Tamao–Corriu coupling polymerization between aryl bromide and Grignard reagents

T. Ohishi, T. Sone, K. Oda and A. Yokoyama, RSC Adv., 2019, 9, 40863
DOI: 10.1039/C9RA08275A

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