Organic OrgCanhiecm istry of Fullerenes-Preparation of Silylmethylated Fullerenes and Their Application to Synthesis of Organic and Inorganic Fullerene Derivatives
1997 Volume 1997 Issue 2 Pages 91-99
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1997 Volume 1997 Issue 2 Pages 91-99
Two types of silylmethylated C60 were prepared by addition of Grignard reagents, ClMgCH2SiY3(Y = alkyl, aryl, alkoxy), to C60. In THF, C60 (H) (CH2SiY3) was formed as a major product, whereas Co (CH2SiY3)2 was selectively produced in toluene. Structures of these compounds were characterized by spectroscopy. Semi-empirical molecular orbital calculations revealed the electronic structures. Redox properties were studied by cyclic voltammetry. Derivatives derived from ClMgCH2Si( CH3)2 [ OCH (CH3)2] were converted to the corresponding chlorosilanes by way of alkoxy exchange of the isoprop oxy group to chlorine atoms with AlCl3 and other chlorinating reagents. The chlorosilanes readily reacted with alcohols in the presence of 2, 6-lutidine with the aid of AgOSO2CF3 to form C60 (H) CH2Si (CH3) 2(OR) and C60[ CH2Si ( CH3)2 (OR)] 2, where R=various alkyl and aryl groups. The chlorosilanes, C60( H )CH2Si (CH3)2 ( Cl), and polyalkoxy silanes, C60( H) CH2Si(CH3)(OR) 3-n, and C60[ CH2Si (CH3)n (OR) 3-n]2, where n= 0 or 1, were useful reagents for surface modification of silica. The modified silica was useful as stationary phases of High Performance Liquid Chromatography or as a heterogeneous photosensitizer. Thermal analysis of a derivative having a cyclic siloxane structure led to successful preparation of its vacuum deposited thin films.
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