PTSA-promoted Dissociation Of Ferrocene Derivatives And Cycloaddition Reaction With Fullerene

Fullerenes and their derivatives have a wide range of applications in optoelectronic materials,biomedicine,and supramolecular chemistry.Therefore,the development of simple and effective methods for functionalizing fullerenes plays an important role in improving the solubility of fullerenes,increasing the diversity of fullerene structures and promoting the reated application.In this dissertation,the p-toluenesulfonic acid-promoted cycloaddition reaction of fullerenes and ferrocene derivatives was studied systematically.By screening different reaction conditions such as acid,temperature and ferrocene derivatives,we explored the effects of different reaction conditions on the reaction.Under the optimal conditions,a series of substrates were examined,and the reaction exhibited a wide range of substrates and good functional group compatibility.After that,we also conducted a useful discussion on the mechanism of the reaction through control experiments and theoretical calculations,and obtained preliminary mechanism information.In addition,the electrochemical properties of the obtained derivatives were tested by cyclic voltammetry,and the results indiacated these derivatives have potential application as acceptors in organic photovoltaic devices.In this work,the ferrocene derivative as a diene synthon has been disclosed for the first time.In the presence of acid,the ferrocene derivatives dissociates effectively,and then undergoes a cycloaddition reaction with fullerenes to form a series of novel [60] fullerene-fused bicyclo[2.2.1]hept-2-ene derivatives derivatives,which are difficult to be prepared by any known literature method.The simple operation of the process,good functional group compatibility,wide substrate scope,high selectivity and yield are its attractive features.