Can the Sidewalls of Single-Wall Carbon Nanotubes Be Ozonized?

Ozonization of the sidewalls of single-wall carbon nanotubes (SWNT) has been investigated by means of 2-layered ONIOM(B3LYP/6-31G*:AM1) calculations. The theoretical calculations reveal that the 1,3-dipolar cycloaddition (1,3-DC) of ozone (O 3 ) onto the sidewalls of a (5,5) carbon nanotube is site-selective and facile with a small activation barrier of 1.4 kcal/mol. The desorption of ozone from the thus-formed ozonide was found to be favorable over the decomposition process that gives rise to epoxy adduct and O 2 upon thermal activation. This work implies the possibility of functionalizing the sidewalls of SWNTs by means of 1,3-dipolar cycloadditions of 1,3-dipolar molecules.