Synthesis of Pentapyrazolyl, Pentapyrrolyl, and Pentaanilino C60 Derivatives

Abstract

Unlike the facile addition of aliphatic amines to fullerenes, heteroaromatic compounds with NH group do not react directly with pristine fullerenes. The present work reports the preparation of several cyclopentadienyl type [60]fullerene derivatives with pyrazole and pyrrole addends through replacement reactions of C60Cl6 in the presence of tetrabutylammonium bromide. The method has also been applied for the synthesis of aniline and methoxyamine [60]fullerene cyclopentadienyl type adducts. Radical species were involved in the reaction mechanism.