Direct Formation of Cycloadducts Between Fullerenes and Amino Acids Through Electron-Transfer Processes

Abstract

The reactions of [60]fullerene and amino acids in the absence of aldehyde in o-dichlorobenzene (ODCB) at 150 °C have been investigated. Fulleropyrrolidines 1 [C₆₀(CH₂N(CH₃)CHC₆H₂(NO₂)₃)], 2 [C₆₀(CH₂N(CH₃)CH₂)], 3 [C₆₀(CH₂NHCH₂)], and 5a–b [C₆₀(RCHNHCHR), R˭CH₃ (5a), R˭CH₂Ph (5b)] were obtained in moderate yields from the reactions of C₆₀ and corresponding amino acids. The reaction of C₇₀ and N-methylglycine in the absence of aldehyde was also studied and was found to give the positional isomers of N-methyl[70]fulleropyrrolidines 6 (1,9-isomer) and 7(7,8-isomer). All products were fully characterized by ultraviolet–visible, Fourier transform–infrared (FT-IR), NMR, and mass spectrometry. The reactions were also carried out in the dark to exclude the possible interference of the photoinduced reactions, and almost the same yields of products were obtained.

GRAPHICAL ABSTRACT

Keywords:

• Amino acids
• cycloaddition reaction
• [60]fullerene
• [70]fullerene
• fulleropyrrolidine

ACKNOWLEDGMENTS

Financial support is provided by the China 863 Program (Project No. 2007AA03Z329), the National Natural Science Foundation of China (Project Nos. 10576026, 10876031, and 50972122), the Sichuan Bureau of Science and Technology of China (Project No. 2008JY0117), and Beijing National Laboratory for Molecular Sciences Fund and Southwest University of Science and Technology Youth Fund (Project No. 10zx3129).