Electrosynthesis and structural characterization of two (C6H5CH2)4C60 isomers

Karl M. Kadish, Xiang Gao, Eric Van Caemelbecke, Tomoyoshi Suenobu, Shunichi Fukuzumi

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The structural, spectral, and electrochemical properties of two (C6H5CH2)4C60 isomers are reported. One is designated as the 1,4; 1,4- (C6H5CH2)4C60 isomer and the other as the 1,4; 1,2-isomer of (C6H5CH2)4C60. The two isomers were isolated by HPLC from the products obtained by a reaction between [(C6H5CH2)2C60]2- and C6H5CH2Br. X- ray data show that the two (C6H5CH2)4C60 isomers differ from one another by the position of only one benzyl group and that, in each compound, the four benzyl addends are in close proximity. Both (C6H5CH2)4C60 isomers undergo three one-electron reductions in PhCN containing 0.1 M tetra- n-butylammonium perchlorate (TBAP) and have E( 1/2 ) values which are more negative than values for either C60 or 1,4-(C6H5CH2)2C60. The monoanions of 1,4;1,4- and 1,4;1,2-(C6H5CH2)4C60 were electrogenerated by bulk controlled-potential electrolysis in PhCN containing 0.2 M TBAP and characterized as to their spectral properties in both the visible and near- infrared regions.

Original languageEnglish
Pages (from-to)563-570
Number of pages8
JournalJournal of the American Chemical Society
Issue number4
StatePublished - 2 Feb 2000


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