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Click synthesis of an adhesive block copolymer with poly(3-hexylthiophene) and poly(vinyl catechol) segments

Polymer Journal (2024)Cite this article

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Abstract

Semiconducting polymers have garnered considerable attention from researchers, as these polymers are potentially applicable to flexible/stretchable organic electronics. However, although the adhesiveness of these materials on substrates is an important characteristic, it has rarely been investigated. Herein, we synthesized and characterized a novel block copolymer, poly(3-hexylthiophene)-b-poly(vinyl catechol) (P3HT-b-PVC), with improved adhesion properties. P3HT-b-PVC was successfully synthesized via a copper-catalyzed azide–alkyne cycloaddition reaction between chain-end-functionalized P3HT with an alkyne group (P3HT-Alkyne) and chain-end-functionalized poly(3,4-di-tert-butyldimethylsilyloxystyrene) with an azide group (PSVC-Azide), followed by deprotection of tert-butyldimethylsilyloxy groups from the PSVC-Azide segment. Tape test results showed that the adhesion property of the P3HT-b-PVC film was considerably better than that of the corresponding P3HT film. Furthermore, despite the presence of an insulating PVC block in P3HT-b-PVC, the P3HT-b-PVC thin film exhibited a hole mobility of 1.1 × 10−5 cm2V−1s−1, which was comparable to that of the corresponding P3HT thin film (1.8 × 10−5 cm2V−1s−1). To the best of our knowledge, this is the first study to elucidate the primitive adhesion properties and charge mobility of P3HT-based block copolymers. The proposed synthetic approach may be extended to develop various block copolymers with other π-conjugated polymer segments, providing new avenues for various applications that require highly-adhesive materials.

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Acknowledgements

This work was supported by Mitsubishi Chemical Corporation. S.I. acknowledges the establishment of university fellowships for the creation of science and technology innovation, grant number JPMJFS2104, and the TEPCO fellowship (20-023) for his financial support.

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Authors and Affiliations

  1. Department of Organic Materials Science, Graduate School of Organic Materials Science, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata, 992-8510, Japan

    Shin Inagaki & Tomoya Higashihara

  2. Mitsubishi Chemical Corporation, Yokohama, Japan

    Kazuhiro Nakabayashi

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  1. Shin Inagaki
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  3. Tomoya Higashihara
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Correspondence to Tomoya Higashihara.

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Inagaki, S., Nakabayashi, K. & Higashihara, T. Click synthesis of an adhesive block copolymer with poly(3-hexylthiophene) and poly(vinyl catechol) segments. Polym J (2024). https://doi.org/10.1038/s41428-024-00898-6

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