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Photochemical Addition of C60 with Siliranes: Synthesis and Characterization of Carbosilylated and Hydrosilylated C60 Derivatives

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posted on 01.09.2010, 00:00 by Junko Nagatsuka, Sachie Sugitani, Masahiro Kako, Tsukasa Nakahodo, Naomi Mizorogi, Midori O. Ishitsuka, Yutaka Maeda, Takahiro Tsuchiya, Takeshi Akasaka, Xingfa Gao, Shigeru Nagase
Photochemical reactions of C60 with siliranes (1ad) afford adducts of four types (2a5b) as carbosilylated and hydrosilylated C60 derivatives. Characterization of these adducts was conducted using MS, UV, NMR spectroscopy, and single-crystal X-ray analyses. In particular, the first example of the crystal structure of a closed 1,2-adduct at the 5,6-ring junction of the C60 cage is provided by single-crystal X-ray analysis of 3b. Electrochemical analyses also revealed unique redox properties of the products 2b5b, which depend on the regiochemistry of the functionality, in addition to the substituents on the C60 cage. Theoretical calculations offer bases for the experimentally observed redox properties and relative stabilities of the silylated products.