Naphthalene Bisimide-Based Acceptor Polymers: Synthesis via Palladium-Catalyzed Direct Arylation, Characterization, and Nanostructure

  • Kazuhiro Nakabayashi
    Department of Polymer Science and Engineering, Graduate School of Science and Engineering, Yamagata University
  • Masaya Yamada
    Department of Polymer Science and Engineering, Graduate School of Science and Engineering, Yamagata University
  • Hideharu Mori
    Department of Polymer Science and Engineering, Graduate School of Science and Engineering, Yamagata University

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<jats:title>Abstract</jats:title> <jats:p>We demonstrated the efficient synthesis of naphthalene bisimide (NBI)-based acceptor polymers by palladium-catalyzed direct arylation, which was a more environmentally friendly and efficient method for the synthesis of conjugated polymers compared to conventional cross-coupling reactions. The direct arylation between our designed thiophene-extended NBI-based monomer and 3,4-dimethylthiophene was successfully carried out to yield the desired NBI-based acceptor polymer (PNBI3T-Dr) with a high molecular weight (Mn &gt; 30000, Mw ≈ 90000) in relatively high yield. The optimal direct arylation could afford the NBI-based acceptor polymer with a higher molecular weight in a shorter reaction time than conventional Stille coupling. Furthermore, grazing incidence wide angle X-ray scattering (GIWAXS) analysis revealed that the as-spun PNBI3T-Dr thin film had π–π stacked nanostructure.</jats:p>

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