Synthesis and Theoretical Studies of Nitryl Fulleropyrrolidine Derivatives
Six nitryl fulleropyrrolidine derivatives were synthesized by the 1,3-dipolar cycloaddition reactions of 60fullerene 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.
60fullerene nitryl fulleropyrrolidine derivatives 1,3-dipolar cycloaddition frontier molecular orbital
金波 彭汝芳 谭碧生 李鸿波 楚士晋
西南科技大学材料科学与工程学院,四川 绵阳 621010 西南科技大学材料科学与工程学院,四川 绵阳 621010;中国工程物理研究院研究生部,四川 绵阳 621900
国际会议
成都
英文
2007-11-19（万方平台首次上网日期，不代表论文的发表时间）