Synthesis And Characterization Of Fullerene Aza-crown Ether And Fullerbenzoylhydrazones Derivatives

The synthesis of novel [60] fullerene derivatives has attracted considerable attention, mainly because of their potential applications in biomedicine, functional materials and energy materials. Researchers use different metal catalyzed molecules or functional groups into the fullerene ball, and get all kinds of functional fullerene derivatives. The palladium-catalyzed C-H bond activation strategy has been successfully applied to fullerene chemistry and several types of [60] fullerene-fused heterocycles and carbocycles have been obtained. However, most of these reactions are require sp2-C lone pair of electrons as directing groups to form [1+3] cycloaddition reaction and subsequent formation of C6o-fused heterocycles, the system has its limitations and are not beneficial to the improvement of open-circuit voltage (Voc). In this paper, we try a simple method using DCU/DCC as catalyst for the synthesis of unreported fullerenes aza crown ether derivative, enriched aza ring fullerene derivatives system. On the other hand, based on the classical C-H activation, different tosylhydrazones with C6o and the use of Cu(OAc)2 as the oxidant in chlorobenzene at 120? under palladium acetate catalyst to give 12 kinds of unreported tosylhydrazones fullerene derivatives, and studied the improved reaction conditions. The structures of obtained products were characterized by FT-IR, UV-vis,1H NMR,13C NMR and MS. Besides, the reaction mechanisms also were discussed.Our work not only enriched the species of functional fullerene derivatives,but also the sp3-C fullerene-catalyzed reaction conditions and the reaction mechanisms were depth studed of, laying a solid foundation for the utilize of functional fullerene derivatives.