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Synthesis of Self-Threading Bithiophenes and their Structure–Property Relationships Regarding Cyclic Side-Chains with Atomic Precision

Authors

  • Yuki Ouchi,

    1. Organic Materials Group, Polymer Materials Unit, National Institute for Materials Science (NIMS), 1-2-1 Sengen, Tsukuba, Ibaraki 305-0047 (Japan), Fax: (+81) 29-859-2101
    2. Department of Materials Science and Engineering, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennoudai, Tsukuba, Ibaraki 305-8571 (Japan)
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  • Dr. Kazunori Sugiyasu,

    Corresponding author
    1. Organic Materials Group, Polymer Materials Unit, National Institute for Materials Science (NIMS), 1-2-1 Sengen, Tsukuba, Ibaraki 305-0047 (Japan), Fax: (+81) 29-859-2101
    • Organic Materials Group, Polymer Materials Unit, National Institute for Materials Science (NIMS), 1-2-1 Sengen, Tsukuba, Ibaraki 305-0047 (Japan), Fax: (+81) 29-859-2101

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  • Dr. Soichiro Ogi,

    1. Organic Materials Group, Polymer Materials Unit, National Institute for Materials Science (NIMS), 1-2-1 Sengen, Tsukuba, Ibaraki 305-0047 (Japan), Fax: (+81) 29-859-2101
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  • Akira Sato,

    1. Materials Analysis Station, National Institute for Materials Science (NIMS)
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  • Prof. Dr. Masayuki Takeuchi

    Corresponding author
    1. Organic Materials Group, Polymer Materials Unit, National Institute for Materials Science (NIMS), 1-2-1 Sengen, Tsukuba, Ibaraki 305-0047 (Japan), Fax: (+81) 29-859-2101
    2. Department of Materials Science and Engineering, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennoudai, Tsukuba, Ibaraki 305-8571 (Japan)
    • Organic Materials Group, Polymer Materials Unit, National Institute for Materials Science (NIMS), 1-2-1 Sengen, Tsukuba, Ibaraki 305-0047 (Japan), Fax: (+81) 29-859-2101

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Abstract

We have recently reported a self-threading polythiophene as a new family of insulated molecular wires. Herein, we focused on the structure–property relationships of the unique three-dimensional architecture of the monomer. We have synthesized nine self-threading bithiophene monomers that have cyclic side-chains of different size and flexibility: i.e., 21-, 22-, 23-, 24-, 26-, and 30-membered rings composed of paraffinic, olefinic, or alkynic chains. To investigate their structure–property relationships, 1H NMR spectroscopy, UV absorption, and fluorescence spectroscopy measurements were conducted. We found that cyclic side-chains define the movable range of the dihedral angle of the bithiophene backbone, thereby affecting its photophysical properties. Therefore, the ability to design a structure with atomic precision as described herein would lead to the fine-tuning of the electronic properties of insulated molecular wires.

Abstract

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