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

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• 作者：Junko Nagatsuka ; Sachie Sugitani ; Masahiro Kako ; Tsukasa Nakahodo ; Naomi Mizorogi ; Midori O. Ishitsuka ; Yutaka Maeda ; Takahiro Tsuchiya ; Takeshi Akasaka ; Xingfa Gao ; Shigeru Nagase
• 刊名：Journal of the American Chemical Society
• 出版年：2010
• 出版时间：September 1, 2010
• 年：2010
• 卷：132
• 期：34
• 页码：12106-12120
• 全文大小：915K
• 年卷期：v.132,no.34(September 1, 2010)
• ISSN：1520-5126

文摘

Photochemical reactions of C₆₀ with siliranes (1a−d) afford adducts of four types (2a−5b) 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 2b−5b, 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.