Silylation of higher fullerenes

Takatsugu Wakahara; AiHong Han; Yasuyuki Niino; Yutaka Maeda; Takeshi Akasaka; Toshiyasu Suzuki; Kazunori Yamamoto; Masahiro Kako; Yasuhiro Nakadaira; Kaoru Kobayashi; Shigeru Nagase

doi:10.1039/B201118B

Takatsugu Wakahara,^a AiHong Han,^a Yasuyuki Niino,^a Yutaka Maeda,^b Takeshi Akasaka,*^b Toshiyasu Suzuki,^c Kazunori Yamamoto,^d Masahiro Kako,^e Yasuhiro Nakadaira,^e Kaoru Kobayashi^c and Shigeru Nagase^c

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* Corresponding authors

^a Graduate School of Science and Technology, Niigata University, Niigata, Japan

^b Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba, Ibaraki, Japan
E-mail: akasaka@tara.tsukuba.ac.jp
Fax: +81-298-53-6409

^c Institute for Molecular Science, Okazaki, Japan

^d Japan Nuclear Fuel Cycle Development Institute, Tokai, Ibaraki, Japan

^e Department of Applied Physics and Chemistry, The University of Electro-Communications, Tokyo, Japan

Abstract

Photochemical silylations of higher fullerenes (C₇₀, C₇₆(D₂), C₈₄(D₂)) are reported. During the photochemical cycloaddition of these higher fullerenes with disilirane, the formation of mono-adducts was observed. Since the highly selective disilirane addition to C₇₀ was observed, the reaction of C₇₆(D₂) and C₈₄(D₂) with disilirane gave at least eight and seven isomers of the mono-adduct, respectively. These adducts were isolated in their pure form by multistage HPLC. The electronic properties of these adducts were also investigated using differential pulse voltammetry. The results indicate that silylation is very effective for producing the electronegative higher fullerene derivatives.

This article is part of the themed collection: Functionalised Fullerenes

Journal of Materials Chemistry

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Silylation of higher fullerenes

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