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Donor–Acceptor Polymers Containing 4,8-Dithienylbenzo[1,2-b:4,5-b′]dithiophene via Highly Selective Direct Arylation Polymerization
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    Donor–Acceptor Polymers Containing 4,8-Dithienylbenzo[1,2-b:4,5-b′]dithiophene via Highly Selective Direct Arylation Polymerization
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    • Masayuki Wakioka*
      Masayuki Wakioka
      International Research Center for Elements Science (IRCELS), Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
      *Email: [email protected]
    • Naohiro Torii
      Naohiro Torii
      International Research Center for Elements Science (IRCELS), Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
    • Masahiko Saito
      Masahiko Saito
      Department of Applied Chemistry, Graduate School of Advanced Science and Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8527, Japan
    • Itaru Osaka
      Itaru Osaka
      Department of Applied Chemistry, Graduate School of Advanced Science and Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8527, Japan
      More by Itaru Osaka
    • Fumiyuki Ozawa
      Fumiyuki Ozawa
      International Research Center for Elements Science (IRCELS), Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
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    ACS Applied Polymer Materials

    Cite this: ACS Appl. Polym. Mater. 2021, 3, 2, 830–836
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    https://doi.org/10.1021/acsapm.0c01163
    Published January 21, 2021
    Copyright © 2021 American Chemical Society

    Abstract

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    While palladium-catalyzed direct arylation polymerization (DArP) is an easy and safe method to synthesize semiconducting polymers with alternating donor–acceptor units (DA polymers), branching and cross-linking defects arising from unintended side reactions are common. When these polymers are used as electronic materials in organic solar cells (OSCs) and similar devices, these defects may adversely affect device performance. We have recently shown that the side reactions can be inhibited by the simultaneous presence of two ligands, P(2-MeOC6H4)3 and N,N,N′,N′-tetramethylethylenediamine (TMEDA). In this study, an efficient donor polymer for OSCs (P1), based on 4,8-dithienylbenzo[1,2-b:4,5-b′]dithiophene (DTBDT) units, was prepared with this mixed-ligand method. The DA polymer is found to exhibit a well-controlled structure, with homocoupling defects of 2.0%, compared to 14.8% observed in the Migita–Stille product (P2). The power conversion efficiency (PCE) was 9.9% when P1 was used, compared to 9.8% for P2 in bulk-heterojunction-type OSC with a nonfullerene acceptor. This demonstrates the effectiveness of the DArP method as a clean and safe alternative method to synthesize DTBDT-based DA polymers for OSCs.

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsapm.0c01163.

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    Cited By

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    This article is cited by 21 publications.

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    ACS Applied Polymer Materials

    Cite this: ACS Appl. Polym. Mater. 2021, 3, 2, 830–836
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acsapm.0c01163
    Published January 21, 2021
    Copyright © 2021 American Chemical Society

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