Highly oxygenated fullerenes by catalytic epoxidation of C60 and single walled carbon nanotubes with methyltrioxorhenium–hydrogen peroxide

Highly oxygenated fullerenes, C60On with 3 ≤ n ≤ 9, have been prepared by the Lewis base enhanced catalytic oxidation of C60 with ReMeO3/H2O2. Pyridine, pyrazole, and 2,2′-bipyridine decrease the activity of the catalyst, while 3-cyanopyridine or 4-bromopyrazole show significant enhancements even at low base:MTO ratios. Increasing the catalyst:C60 ratio increases the yield as well as shifting the product distribution to higher oxygenated products, in contrast, increasing the H2O2 concentration or increasing the reaction temperature shifts the product distribution in the opposite manner. Epoxidation of single walled carbon nanotubes (SWNTs) is accomplished with ReMeO3/H2O2/4-bromopyrazole.

Graphical abstractHighly oxygenated fullerenes, C60On with 3 ≤ n ≤ 9, have been prepared by the Lewis base enhanced catalytic oxidation of C60 with ReMeO3/H2O2. Pyridine, pyrazole, and 2,2′-bipyridine decrease the activity of the catalyst, while 3-cyanopyridine or 4-bromopyrazole show significant enhancements. Epoxidation of single walled carbon nanotubes (SWNTs) is accomplished with ReMeO3/H2O2/4-bromopyrazole.Figure optionsDownload full-size imageDownload as PowerPoint slide