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

J. Simonet (1) , V. Jouikov (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

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 C60 4−, 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.

Keywords: Electrophiles; Carboxylation; Tetramethylammonium salts; Solid substrates; Polar aprotic solvent; Electrophilic reagents; Fullerene C60; High reactivity; Anodic oxidation; Carbon dioxide; Dimethylformamide; Fullerenes; Glass; Glassy carbon; Gold deposits; Organic solvents; Dicarboxylates

Domains: Chemical Sciences; Material chemistry

J. Simonet, V. Jouikov. Immobilization of fullerene C60 at cathodically polarized glassy carbon for generation of thin nucleophilic layers and their carboxylation and alkylation. Carbon, 2020, 156, pp.438-444. ⟨10.1016/j.carbon.2019.09.060⟩. ⟨hal-02367955⟩