Aromatic electron acceptors change the chirality dependence of single-walled carbon nanotube oxidation

Single-walled carbon nanotubes (SWNTs) dispersed in sodium dodecyl sulfate (SDS) suspensions exhibit diameter-dependent protonation and oxidative quenching of their E11 fluorescence. This nanotube-diameter-based difference in solution chemistry is substantially changed when complexed with aromatic electron-accepting compounds such as nitrobenzene, o-nitrotoluene, 2,4-dinitrotoluene, and 9-nitroanthracene. SWNTs were suspended in aqueous SDS, and their emission spectra were measured as a function of pH and concentration of oxidizing agent (hypochlorite or hydrogen peroxide) to observe their protonation and oxidation behavior. The chirality dependence of the protonation and oxidation behavior became substantially reduced upon the addition of nitroaromatic compounds to the aqueous suspension. This suggests the possibility of forming an electron donor-acceptor (EDA) complex, where the SWNT is the electron donor and nitroaromatic compounds are the acceptor, and the resulting supramolecular complex exhibits different redox behavior than the uncomplexed SWNT.