An isomer of C60Cl10 free of skew-pentagonal-pyramidal C60Cl6 substructure.

Chlorination is an effective approach for understanding the feature of multiple additions on fullerene cages. The chlorofullerenes obtained are versatile synthons for further derivatization. However, chlorofullerenes used for chemical reaction studies are mainly based on the skew-pentagonal-pyramidal (SPP) C60Cl6. In this work, a new isomer of C60Cl10 that does not contain an SPP-C60Cl6 substructure was identified. Its electrochemical properties give it unexpected cyclic voltammetric behavior at more negative potentials relative to other chlorofullerenes. Friedel-Crafts arylation shows good reactivity of this compound. These new findings challenge opinions of fullerene addition patterns and will break the monopoly of C60Cl6 as a precursor for fullerene modifications.