Synthesis and Theoretical Studies of Nitryl Fulleropyrrolidine Derivatives

摘要

Six nitryl fulleropyrrolidine derivatives were synthesized by the 1,3-dipolar cycloaddition reactions of [60]fullerene with various nitrophenyl azomethine ylides and the nucleophilic substitution reaction of nitryl benzene halide to 2-(3-nitrophenyl)fulleropyrrolidine 1. The structures of these compounds were verified by UV-vis, FT-IR, 1H NMR, 13C NMR and MS. The different 1,3-dipole showed different reactivity in the cycloaddition reaction, and it was rationalized by frontier molecular orbital theoretical points of views based on parameterization model 3 (PM3) calculations. The calculation results showed that the different LUMO(fullerene)-HOMO(dipole) energy gap of various 1,3-dipoles was the principal reason, and the higher reactivity was corresponded to a small LUMO(fullerene)-HOMO(dipole) energy gap.