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Tetracene Dicarboxylic Imide and Its Disulfide: Synthesis of Ambipolar Organic Semiconductors for Organic Photovoltaic Cells

Authors

  • Dr. Toshihiro Okamoto,

    Corresponding author
    1. Department of Chemistry, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-1476
    2. Present address: Department of Advanced Electron Devices , Institute of Scientific and Industrial Research (ISIR) , 8-1 Mihogaoka, Ibaraki, Osaka 567-0047 (Japan)
    • Department of Chemistry, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-1476

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  • Tsuyoshi Suzuki,

    1. Department of Chemistry, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-1476
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  • Dr. Hideyuki Tanaka,

    1. Department of Chemistry, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-1476
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  • Dr. Daisuke Hashizume,

    1. Advanced Technology Support Division, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan)
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  • Prof. Yutaka Matsuo

    Corresponding author
    1. Department of Chemistry, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-1476
    • Department of Chemistry, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-1476

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Abstract

We have designed and synthesized a new donor/acceptor-type tetracene derivative by the introduction of dicarboxylic imide and disulfide groups as electron-withdrawing and -donating units, respectively. The prepared compounds, tetracene dicarboxylic imide (TI) and its disulfide (TIDS) have high chemical and electrochemical stability as well as long-wavelength absorptions of up to 886 nm in the thin films. The crystal packing structure of TIDS molecules features face-to-face π-stacking, derived from dipole–dipole interactions. Notably, TIDS exhibited ambipolar properties of both electron-donating and -accepting natures in pn and p–i–n heterojunction organic thin-film photovoltaic devices. Accordingly, TI and TIDS are expected to be promising compounds for designing new organic semiconductors.

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