Synthesis and spectroscopic and electrochemical characterization of di- and tetrasubstituted C60 derivatives

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

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Abstract

The synthesis and electrochemical and spectroscopic characterization of fullerene derivatives of the type R2C60 where R = C6H5CH2, 2-BrC6H4CH2, 3-BrC6H4CH2, or 4-BrC6H4CH2 and R4C60 where R = C6H5CH2 are reported. The first step in the synthesis involves an electron transfer between C602- and RBr, and a similar initial electron-transfer step occurs between [(C6H5CH2)2C60] 2- and C6H5CH2Br during the synthesis of (C6H5CH2)4C60. On the basis of NMR and UV - visible data, the investigated R2C60 derivatives are identified as 1,4-adducts of C60, whereas the isolated isomer of (C6H5CH2)4C60 is characterized as possessing C1 symmetry with the four benzyl groups being close to each other. The electrochemistry of each synthesized compound was determined in benzonitrile containing 0.1 M tetra-n-butylammonium perchlorate and each mono- and dianion of R2C60 and R4C60 were characterized by near-infrared spectroscopy. The near-infrared spectra of each species show two major "marker bands" which can be considered to be diagnostic of the fullerene derivative oxidation state.

Original languageEnglish
Pages (from-to)3898-3906
Number of pages9
JournalJournal of Physical Chemistry A
Volume102
Issue number22
DOIs
StatePublished - 28 May 1998

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