Immobilization of fullerene C60 at cathodically polarized glassy carbon for the generation of thin nucleophilic layers and their carboxylation and alkylation

Abstract

Listen

Translate article

Fullerene-C60 deposited onto solid substrates (glassy carbon, gold) was polarized between 0 V and −2 V vs. Ag/AgCl/KClsat (aq) in polar aprotic solvents (dimethylformamide or acetonitrile) containing tetramethylammonium salts in the presence of electrophilic reagents, namely primary haloalkanes (Hal = Br, I) and carbon dioxide. The electrogenerated reduced forms of C60 (C60− to C604−, fullerene polyanions), show high reactivity towards various electrophiles which permits preparing C60 dicarboxylates whose formation was established through coulometric integration. Importantly, anodic oxidation (Ep ≈ +1 V) of thus produced C60 dicarboxylates led to the complete regeneration of C60 via a Kolbe bis-decarboxylation.