| Tether-directed selective synthesis of fullerene multiple adducts is a key step in the study of their properties and applications. This thesis describes our novel approach for tether-controlled multiple functionalization of fullerenes through nucleophilic cyclopropanation of malonates and azomethine ylide [3+2] cycloaddition, reactions known as the Bingel-Hirsch reaction and the Prato reaction. Macrocyclic polyether fullerenes with defined three-dimension geometry are prepared using tether-directed bis- and tris-cyclopropanation, and they are a new class of ionophores. Our tether-directed double Prato reactions to C60 provide a general approach to prepare bisadducts with high selectivity and yield. This is the first systematic study of selective synthesis of fulleropyrrolidine bisadducts.;Fullerene-metal interaction is a major topic in fullerene chemistry and it is very important for fullerene applications in molecular recognition, electron transfer, and self-assembled molecular architectures. A number of fullerene ligands have been designed and synthesized using the above mentioned approaches and their complexation with both soft and hard metals are reported in this thesis. |
