화학공학소재연구정보센터
Journal of Physical Chemistry A, Vol.102, No.22, 3898-3906, 1998
Synthesis and spectroscopic and electrochemical characterization of di- and tetrasubstituted C-60 derivatives
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 C-60(2-) and RBr, and a similar initial electron-transfer step occurs between [(C6H5CH2)(2)C-60](2-) and C6H5CH2Br during the synthesis of (C6H5CH2)(4)C-60. On the basis of NMR and UV-visible data, the investigated R2C60 derivatives are identified as 1,4-adducts of C-60, whereas the isolated isomer of (C6H5CH2)(4)C-60 is characterized as possessing C-1 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.