Separation of semiconducting from metallic carbon nanotubes by selective functionalization with azomethine ylides

A mild and efficient method for the functionalization of SWNTs by cycloaddition of azomethine ylides derived from trialkylamine-N-oxides is described. Selective reaction of semiconducting carbon nanotubes was achieved by preorganizing the starting N-oxides on the nanotube surface prior to generating the reactive ylides. Separation of met-SWNTs from functionalized sem-SWNTs was successfully accomplished by inducing solubilization of sem-SWNTs in the presence of lignoceric acid.