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Selective Functionalization of Fullerenes with N,N-Dihalosulfonamides as an N1 Unit: Versatile Syntheses of Aza[60]fulleroids and Aziridino[60]fullerenes and their Application to Photovoltaic Cells

Authors

  • Toshiki Nagamachi,

    1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-8402
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  • Dr. Youhei Takeda,

    1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-8402
    2. Frontier Research Base for Global Young Researchers, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan)
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  • Kazuhisa Nakayama,

    1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-8402
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  • Prof. Dr. Satoshi Minakata

    Corresponding author
    1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-8402
    • Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-8402
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Abstract

Highly selective and versatile methods for the synthesis of aza[60]fulleroids and aziridino[60]fullerenes from C60 have been developed. The reactions utilized N,N-dihalosulfonamides as an N1 source. The photophysical, electrochemical, and thermal properties of the iminofullerenes were investigated by means of UV/Vis spectroscopy, cyclic voltammetry, and thermogravimetry, respectively. Furthermore, photovoltaic cells based on the synthesized iminofullerenes were fabricated. The power conversion efficiencies (PCEs) of the devices showed moderate values ranging from 1.33 to 2.35 %.

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