Photochemical addition of C60 with siliranes: synthesis and characterization of carbosilylated and hydrosilylated C60 derivatives.
Photochemical reactions of C(60) with siliranes (1a-d) afford adducts of four types (2a-5b) as carbosilylated and hydrosilylated C(60) 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 C(60) 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 C(60) cage. Theoretical calculations offer bases for the experimentally observed redox properties and relative stabilities of the silylated products.
Nagatsuka
Junko
J
Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Tsukuba 305-8577, Japan.
Sugitani
Sachie
S
Kako
Masahiro
M
Nakahodo
Tsukasa
T
Mizorogi
Naomi
N
Ishitsuka
Midori O
MO
Maeda
Yutaka
Y
Tsuchiya
Takahiro
T
Akasaka
Takeshi
T
Gao
Xingfa
X
Nagase
Shigeru
S
D037741:Fullerenes / Q000737:chemistry*; D015394:Molecular Structure; D010777:Photochemistry; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D037741:Fullerenes; D012821:Silanes; C069837:fullerene C60