title: Electrosynthesis and characterization of 1,2-dibenzyl C60: a revisit.
abstract: A reinvestigation of the reaction between C60(2-) and benzyl bromide in benzonitrile containing 0.1 M tetra-n-butylammonium perchlorate (TBAP) has shown that there are more reaction products than previously reported. Use of a silica rather than a "Buckyclutcher I" column for HPLC purification led to isolation of two previously unattained products in the reaction mixture, one of which was identified as 1,2-(PhCH2)2C60 by UV-vis and NMR . The earlier incorrectly assigned 1,2-(PhCH2)2C60 was identified as the methanofullerene C61HPh by X-ray single-crystal diffraction. The electrochemistry of genuine 1,2-(PhCH2)2C60 shows that its first reduction potential in PhCN containing 0.1 M TBAP is cathodically shifted by 100 mV with respect to E1/2 for reduction of 1,4-(PhCH2)2C60, indicating that the addition pattern significantly affects the electrochemistry of derivatized C60. Visible and near-IR spectra of the monoanion and dianion of 1,2-(PhCH2)2C60 are also reported.
authors.affiliation: State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Graduate School of Chinese Academy of Sciences, Chinese Academy of Sciences, Changchun, Jilin 130022, China.
authors.forename: Min
authors.initials: M
authors.lastname: Zheng
authors.forename: Fangfang
authors.initials: F
authors.lastname: Li
authors.forename: Zujin
authors.initials: Z
authors.lastname: Shi
authors.forename: Xiang
authors.initials: X
authors.lastname: Gao
authors.forename: Karl M
authors.initials: KM
authors.lastname: Kadish