Photodegradation of anthracene and benzo[a]anthracene in polar and apolar media: new pathways of photodegradation

The photochemical reactions of anthracene and benzo[a]anthracene polycyclic aromatic hydrocarbons (PAHs) in polar and apolar solvents (cyclohexane and water/acetonitrile) were studied using spectroscopic and chromatographic techniques. These homogenous photolysis experiments are used as simplified models to compare PAHs photochemistry in water and oil (or oil films). Moreover, these processes were to some extent used as model in literature in order to study those occurring on particulate matter and aerosol surfaces. In both media, new photochemical reaction products were found. Generally, the reaction rate in the polar medium is faster than that in the apolar medium, and the photodegradation quantum yields increase with increasing polarity of the medium. HPLC-absorption/emission analysis confirmed the literature reports that mainly oxygenated photoproducts, such as PAH-hydroxides, were formed. The novelty of this paper is that GC-MS data revealed the presence of new photoproducts that have not yet been described. This simplified model system allowed us to characterize the product distribution, thus simplifying the interpretation of the photodegradation mechanism. The identification of new photofragmentation paths, originating by irradiation of primary PAH photoproducts, may suggest an innovative way of remediation triggered by light.