Journal of the American Chemical Society, Vol.120, No.45, 11645-11648, 1998
Enhanced acceptor character in fullerene derivatives. Synthesis and electrochemical properties of fulleropyrrolidinium salts
A family of N-methylpyrrolidinium fullerene iodide salts, possessing one (or two) solubilizing chain(s), has been synthesized. As evidenced by CV and steady-state voltammetry experiments, carried out in tetrahydrofuran (THF) solutions, these species show enhanced electron-accepting properties with respect to both the parent fulleropyrrolidines and C-60 CV measurements performed at -60 degrees C and scan rates of 50 V/s, made possible by the use of ultramicroelectrodes, : have allowed the observation, for the first time in fullerene derivatives, of six fullerene-centered reductions. Bulk electrolysis of these novel compounds, performed at the stage of the first reduction potential, generates a stable zwitterion, with both anion and cation located on the fullerene derivative.
Keywords:PHOTOINDUCED ELECTRON-TRANSFER, NEGATIVE POTENTIALS, CYCLICVOLTAMMETRY, AZOMETHINE YLIDES, C-60, BUCKMINSTERFULLERENE;FULLEROIDS, METHANOFULLERENES, REDUCTION, FILMS