Base-promoted reaction of C60Cl6 with thioamides: an access to [60] fullereno[1,9-d] thiazoles

Abstract

Regioselective reaction of C60Cl6 with thioamides via a radical annulation to form fullereno thiazole derivatives is reported. The reaction is promoted by K2CO3, which might deprotonate thioamide to initiate a single electron transfer from thioamide anion to C60Cl6. The experiments with various thioamides establish the proposed base-promoted reaction as a facile route for synthesis of fullereno fused thiazole derivatives starting from C60Cl6, a prevalent synthon in fullerene chemistry. In addition, the tunable electrochemical properties of the fullereno thiazole products have been investigated for their potential photovoltaic application. (C) 2014 Elsevier Ltd. All rights reserved.