Tunable Epoxidation of Single-Walled Carbon Nanotubes by Isolated Methyl(trifluoromethyl)dioxirane

Organic functionalization of carbon nanotube sidewalls is a tool of primary importance in material science and nanotechnology, equally from a fundamental and an applicative point of view. In this paper, a mild and easily tunable approach to the sidewall decoration of single-walled carbon nanotubes (SWCNTs) with epoxides and their subsequent derivatization (ring opening) upon treatment with reactive nucleophiles is presented. The treatment of HiPco purified SWCNTs with dioxirane solutions results in highly oxidized CNTs, which are used as electrophilic platforms for their successive derivatization/functionalization. As a result of the choice of accessible, easy to handle and store dioxiranes, multiple oxidation cycles could be performed on the same sample, thus allowing for a final improvement in the extent of oxidation at the CNT sidewall.