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Detailed Optimization of Polycondensation Reaction via Direct C–H Arylation of Ethylenedioxythiophene

Authors

  • Koutarou Yamazaki,

    1. Tsukuba Research Center for Interdisciplinary Materials Science (TIMS), Graduate School of Pure and Applied Science, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8573, Japan
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  • Junpei Kuwabara,

    1. Tsukuba Research Center for Interdisciplinary Materials Science (TIMS), Graduate School of Pure and Applied Science, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8573, Japan
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  • Takaki Kanbara

    Corresponding author
    1. Tsukuba Research Center for Interdisciplinary Materials Science (TIMS), Graduate School of Pure and Applied Science, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8573, Japan
    • Tsukuba Research Center for Interdisciplinary Materials Science (TIMS), Graduate School of Pure and Applied Science, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8573, Japan.
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Abstract

The polycondensation reaction of 3,4-ethylenedioxythiophene with 2,7-dibromo-9,9-dioctylfluorene via Pd-catalyzed direct arylation gives poly[(3,4-ethylenedioxythiophene-2,5-diyl)-(9,9-dioctylfluorene-2,7-diyl)]. The reaction conditions are optimized in terms of the Pd precatalysts, reaction time, and carboxylic acid additives. The combination of 1 mol% Pd(OAc)2 and 1-adamantanecarboxylic acid as an additive is the optimized catalytic system, and it yields the corresponding polymer with a molecular weight of 39 400 in 89% yield. The polycondensation reaction, followed by an end-capping reaction, effectively provides a linear polymer without Br terminals.

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