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The Catalytic Oxidative Polymerization of 3-Hexylthiophene by Oxidation of Fe2+ to Fe 3+

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Abstract

In the case of the oxidative polymerization of 3-hexylthiophene (3HT) with FeCl3, FeCl3 is always required at a concentration four times higher than that of 3HT to produce high-molecular-weight P3HT. In order to avoid the use of excess FeCl3, it was considered that an oxidizer could assist the catalytic oxidative polymerization by oxidizing Fe2+ to Fe3+. To determine an effective oxidation agent (Fe2+ to Fe3+), various oxidizers (Cl2, BPO, H2O2, ZrCl4, and (NH4)2Ce(NO3)6) were examined. The obtained results indicated that Ce4+ was the most effective oxidant among those tried for the polymerization of 3HT. The polymer yield was typically 29–35% without the addition of (NH4)2Ce(NO3)6, but the yield improved to 53% with it. To confirm whether Fe2+ was oxidized to Fe3+ by Ce4+, a combination of Fe2+ and Ce4+ was used to perform an oxidative polymerization of 3HT. As a result, poly(3-hexylthiophene) was successfully obtained with the combination of FeCl2 and (NH4)2Ce(NO3)6 as oxidative agents. This result indicates that Fe3+ was formed by the oxidation of Fe2+ with Ce4+, followed by catalytic oxidative polymerization.

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Authors and Affiliations

  1. School of Environmental Science and Engineering, Kochi University of Technology, Miyanokuchi, Tosayamada, Kami, Kochi, 782-8502, Japan

    Thien An Phung Hai & Ryuichi Sugimoto

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  1. Thien An Phung Hai
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  2. Ryuichi Sugimoto
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Correspondence to Ryuichi Sugimoto.

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Hai, T.A.P., Sugimoto, R. The Catalytic Oxidative Polymerization of 3-Hexylthiophene by Oxidation of Fe2+ to Fe 3+ . Catal Lett 147, 1955–1965 (2017). https://doi.org/10.1007/s10562-017-2117-2

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  • DOI: https://doi.org/10.1007/s10562-017-2117-2

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