Benzo[c]thiophene–C60 Diadduct: An Electron Acceptor for p–n Junction Organic Solar Cells Harvesting Visible to Near-IR Light

Authors

  • Dr. Yonggang Zhen,

    1. Department of Chemistry, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81)-3-5800-6889
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  • Dr. Naoki Obata,

    1. Department of Chemistry, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81)-3-5800-6889
    2. Mitsubishi Chemical Group Science and Technology Research Center, Inc. 1000 Kamoshida-cho, Yokohama 227-8502 (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)-3-5800-6889
    • Department of Chemistry, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81)-3-5800-6889

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  • Prof. Eiichi Nakamura

    Corresponding author
    1. Department of Chemistry, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81)-3-5800-6889
    • Department of Chemistry, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81)-3-5800-6889

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Abstract

We synthesized a new 56-π-electron fullerene derivative through a Diels–Alder cycloaddition of benzo[c]thiophene that featured a relatively low temperature, closer to stoichiometric use of the diene, and easy product purification. The 56-π-electron benzo[c]thiophene diadduct (BTCDA) has a LUMO energy level of 0.09 to 0.18 eV higher than that of 58-π-electron fullerenes, and therefore, the BTCDA-based organic photovoltaic device exhibited a higher open-circuit voltage and power-conversion efficiency (PCE). When used with a binary-donor system, including visible-light-harvesting tetrabenzoporphyrin (BP) and near-IR-harvesting titanyl phthalocyanine (TiOPc), the device had a PCE that was 1.5–3 times higher (2.8 %) than that for devices with BP or TiOPc alone because the binary-donor device can utilize light between λ=350 and 950 nm.

Abstract

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