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Postfunctionalization of the main chain of Poly(3-hexylthiophene) via anodic C–H phosphonylation

Polymer Journal volume 54, pages 1171–1178 (2022)Cite this article

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Abstract

Postfunctionalization of aromatic C – H bonds at the main chains of π-conjugated polymers (CPs) is ideal for tuning various functionalities of precursor CPs because aromatic C – H bonds are the most common structures in their backbone. However, C – H activation reactions available in postfunctionalization methods remain limited. Here, we expand this limitation by performing electrochemical C – H phosphonylation of the main chain of poly(3-hexylthiophene) (P3HT). The introduction of phosphonate moieties into the main chain of CPs is potentially useful for improving their processibilities and imparting sensing abilities to them. Anodic phosphonylation of P3HT was successfully achieved using trialkyl phosphite as an electrically neutral nucleophile in the presence of nonnucleophilic dopants. The chemical structures and the optoelectronic properties of phosphonylated P3HT were characterized.

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Funding

This work was supported by Kakenhi Grants-in-Aid (JP19J23415 and JP20H02796) from the Japan Society for the Promotion of Science (JSPS) and a Support for Tokyo Tech Advanced Researchers [STAR] grant funded by the Tokyo Institute of Technology Fund (Tokyo Tech Fund).

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Authors and Affiliations

  1. Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8502, Japan

    Kohei Taniguchi, Tomoyuki Kurioka, Ikuyoshi Tomita & Shinsuke Inagi

  2. Graduate School of Science and Engineering, Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku, Yokohama, 240-8501, Japan

    Naoki Shida

  3. PRESTO, Japan Science and Technology Agency (JST), 4-1-8 Honcho, Kawaguchi, Saitama, 332-0012, Japan

    Shinsuke Inagi

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  1. Kohei Taniguchi
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Correspondence to Shinsuke Inagi.

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Taniguchi, K., Kurioka, T., Shida, N. et al. Postfunctionalization of the main chain of Poly(3-hexylthiophene) via anodic C–H phosphonylation. Polym J 54, 1171–1178 (2022). https://doi.org/10.1038/s41428-022-00671-7

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