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Open-Cage Fullerene Derivatives: Synthesis, Reactions, and Encapsulation of a Small Molecule

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Chemical Science of π-Electron Systems

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Abstract

The synthetic methods to create a large opening on the fullerene C60 cage are developed. A water molecule was encapsulated into the open-cage C60 derivative, and the opening was completely restored to afford H2O@C60 in a macroscopic scale under the mild reaction conditions. To realize an encapsulation of a large molecule, efficient way to create a larger opening is found by the reaction with nucleophilic oxidants, which was also applied to a precursor of azafullerenes, in which one of the carbon atoms in fullerene cages is replaced with a nitrogen atom. As another method to enlarge the opening, a sulfur atom was introduced on the rim of the openings. When this reaction was applied to an open-cage C60 derivative, a new open-cage C59S derivative was obtained in addition to the expected compound having a larger opening. Furthermore, when this reaction was applied to an open-cage C70 derivative, another new reaction was found to afford an open-cage C69S derivative. In this chapter, synthetic methods are described for these new carbon-cage molecular systems, including endohedral fullerenes, open-cage fullerenes encapsulating a molecule, and open-cage heterofullerene derivatives.

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Authors and Affiliations

  1. Institute for Chemical Research, Kyoto University, Uji, Japan

    Yasujiro Murata

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  1. Yasujiro Murata
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Correspondence to Yasujiro Murata .

Editor information

Editors and Affiliations

  1. Foundation for Advancement of International Science, Tsukuba, Japan

    Takeshi Akasaka

  2. Kyoto University, Kyoto, Japan

    Atsuhiro Osuka

  3. Department of Chemistry and Nano Science,, Ewha Womans University, Seoul, Korea (Republic of)

    Shunichi Fukuzumi

  4. Nagoya Institute of Technology, Nagoya, Japan

    Hideki Kandori

  5. Osaka University, Suita, Japan

    Yoshio Aso

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Murata, Y. (2015). Open-Cage Fullerene Derivatives: Synthesis, Reactions, and Encapsulation of a Small Molecule. In: Akasaka, T., Osuka, A., Fukuzumi, S., Kandori, H., Aso, Y. (eds) Chemical Science of π-Electron Systems. Springer, Tokyo. https://doi.org/10.1007/978-4-431-55357-1_8

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