Synthesis and electrochemical properties of ionic fullerene derivatives Original Research Article

1,3-Dipolar cycloaddition of azomethine ylides to C60 generates a family of fullerene derivatives, colloquially termed fulleropyrrolidines. In this paper, we report the synthesis and the electrochemical properties of fulleropyrrolidine and fulleropyrrolidinium ion derivatives. Cyclic voltammetry measurements, performed using ultramicroelectrodes at −60°C with scan rates as high as 50 V/s, allowed, for the first time in fullerene derivatives, the observation of six fullerene-centered reductions. These derivatives also exhibit enhanced electron-accepting properties with respect to both the parent fulleropyrrolidine derivatives and C60. Bulk electrolysis carried out at the stage of the first reduction potential, gives rise to a stable zwitterion, with both anion and cation located on the fullerene derivatives.