Synthesis Of CuI-Promoted Novel Methanofullerene And C₆₀-Fusde Cyclic1,2-Diaminated Derivatives

Since the discovery of fullerenes by Kroto and Smalley in 1985,the chemical modifications of fullerenes have received important attention.To date,various fullerene derivatives have been synthesized,and they exhibit wide application in materials science,life medicine,and host-guest chemistry.Therefore,it is important to develop a simple and efficient method to construct novel[60]fullerene derivatives.In this dissertation,a simple and efficient synthetic method access to novel methanofullerenes and C₆₀-fused cyclic 1,2-diaminated derivatives have been developed.The reactions were promoted by CuI under mild conditions.The optimal reaction conditions were obtained by screening different copper salts,bases,temperatures,and the amount of substrate.Based on the optimal conditions,the scope of substrates was extended and the electronic and steric effects of the reaction substrate were disscussed,and the reaction mechanism was proposed.In addition,the electrochemical properties of new-obtained representative[60]fullerene derivatives and C₆₀-fused cyclic 1,2-diaminated derivatives were investigated and the results indicated that such derivatives have potential applications as acceptors in organic photovoltaic devices.In summary,we have developed a simple and efficient method for the synthesis of novel methanofullerenes and C₆₀-fused cyclic 1,2-diaminated derivatives,which have the advantages of readily availability of substrates,operational simplicity,mild conditions and high atom economical efficiency.