Synthesis, Characterization and Theoretical Calculation of the Fulleropyrrolidines Containing Triphenylamine

Abstract

AbstractN‐Methyl‐2‐(4‐N,N‐diphenylaminophenyl)fulleropyrrolidine and N‐methyl‐2‐(4‐di‐p‐tolylaminophenyl)fulleropyrro‐ lidine were synthesized via the 1,3‐dipolar cycloaddition reactions under microwave irradiation. The molecular structures were identified and characterized by MS, UV‐Vis, FT‐IR, 1H NMR and fluorescence spectra. Photoinduced intramolecular electron transfer process from C60 moiety to triphenylamine moiety have been studied by nanosecond laser flash photolysis. The optimized structure and the distribution of the frontier molecular orbitals for C60‐TPA were obtained by using DFT method at B3LYP/6‐31G(d) level. The results indicated that the intramolecular photoinduced electron transfer could occur in these compounds, which were in excellent agreement with the nanosecond transient absorption spectra observed experimentally in polar solvent. The electronic spectrum of the compound C60‐TPA was studied by ZINDO method on the basis of the optimized geometrics, which was essentially consistent with experimental values.