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Precision synthesis of regioregular poly(3-hexylthiophene) with low dispersity using a zincate complex catalyzed by nickel with the ligand of 1,2-bis(dicyclohexylphosphino)ethane

Authors

  • Eisuke Goto,

    1. Department of Polymer Science and Engineering, Graduate School of Science and Engineering, Yamagata University, Jonan, Yonezawa, Japan
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  • Saki Nakamura,

    1. Department of Organic and Polymeric Materials, Graduate School of Science and Engineering, Tokyo Institute of Technology, Meguro-Ku, Tokyo, Japan
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  • Susumu Kawauchi,

    1. Department of Organic and Polymeric Materials, Graduate School of Science and Engineering, Tokyo Institute of Technology, Meguro-Ku, Tokyo, Japan
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  • Hideharu Mori,

    1. Department of Polymer Science and Engineering, Graduate School of Science and Engineering, Yamagata University, Jonan, Yonezawa, Japan
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  • Mitsuru Ueda,

    1. Department of Polymer Science and Engineering, Graduate School of Science and Engineering, Yamagata University, Jonan, Yonezawa, Japan
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  • Tomoya Higashihara

    Corresponding author
    1. Department of Polymer Science and Engineering, Graduate School of Science and Engineering, Yamagata University, Jonan, Yonezawa, Japan
    2. Japan Science and Technology Agency (JST), Kawaguchi, Saitama, Japan
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ABSTRACT

Regioregular poly(3-hexylthiophene) (P3HT) has been a commonly used p-type semiconducting material for solution processable organic electronics. To establish a living system of “Negishi-type catalyst-transfer polycondensation (NCTP)” using zincate complex as a synthetic method for well-defined P3HT having predictable molecular weight (MW) and low dispersity (Đ), the ligands of Ni catalyst were optimized. As a result, a ligand of 1,2-bis(dicyclohexylphosphino)ethane produced P3HTs with highly controlled number average MWs (1650–32,800) and very low Đ values (1.03–1.17). The polymerization results were strongly influenced by steric hindrance based on the factors of cone angle and bite angle of Ni catalysts, and/or electron-donating ability of phosphine ligands. In addition, we succeeded in the two-stage polymerization of P3HT and the synthesis of P3HT-b-poly(3-octadecylthiophene), the latter of which is the first demonstration by NCTP using zincate complex. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 2287–2296

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