Ozonolysis of polycyclic aromatic hydrocarbons in participating solvents

Abstract

Seven polycyclic aromatic hydrocarbon (PAH) compounds that can be considered small models for graphene edges have been treated with ozone in solution. The presence of participating solvents such as water or methanol had a pronounced influence on conversion and identity of the functional groups formed, whereas the regioselectivity of the ozonation remained unaffected. Six previously unreported compounds have been isolated from the ozonolysis of pyrene 1, perylene 2 and benzo[e]pyrene 4. Comparison of the experimental data with calculated local ionization energy surfaces (IES) shows a good correlation, and indicates that this computational tool would be useful to predict the regioselectivity of ozone also for larger PAHs, including graphene and graphene nanoribbons.