Synthesis of fullerene building blocks bearing alkyne or azide groups and their subsequent functionalization by the copper mediated Huisgen 1,3-dipolar cycloaddition

C-60 derivatives bearing either terminal alkyne or azide functional groups have been prepared and used as building blocks under the copper mediated Huisgen 1,3-dipolar cycloaddition conditions. In general, the reactivity of C60 toward azides does not significantly compete with the cycloaddition leading to the desired 1,2,3-triazole derivatives and good yields can be obtained when fullerene derivatives with reasonable Solubility are used as starting materials. The electrochemical properties of the new fullerene derivatives have also been investigated by cyclic voltammetry (CV) and Osteryoung Square Wave Voltammetry (OSWV). (C) 2008 Elsevier Ltd. All rights reserved.