Syntheis Of [60]Fullerene-Tetrahydrocyclope NTA[2,3-b]Indoles Derivatives

Since the discovery of fullerenes in 1985,the skeleton modification of fullerenes has been a hot research area.To date,a variety of fullerene derivatives with novel structures and unique functions have been synthesized and widely used in fields such as solar cells,biomedicine,nanomaterials,and photoelectric materials.Therefore,the development of simple and efficient new methodes for the chemical modification of fullerenes leading to diverse[60]fullerene derivatives with novel structure is crucial.This dissertation developed the direct copper-catalyzed oxidative dehydrogenative radicalcarbocyclication for the construction of novel[60]fullerene-fused tetrahydrocyclopenta[2,3-b]indoles.By screening various copper salts,bases,peroxides,and their amounts,reaction timesand temperatures,we determined the optimal reaction conditions.Under the optimal reaction conditions,we expanded the substrate and discussed the electronic and steric effects of substituents on the reaction.A series of control experiments were carried out to clarify the reaction mechanism.In addition,we investigated the electrochemical properties of new-obtained representative derivatives,and similar redox potentials compared to[6,6]-Phenyl-C₆₁-methylbutyrate?PCBM?were observed,indicating these new type fullerene carbocyclic adducts have potential application as acceptors in organic photovoltaic devices.In conclusion,this dehydrogenative coupling reaction exhibits high atom economy,broad substrate scope,and good functional group compatibility.