Monofluorinated Polycyclic Aromatic Hydrocarbons: Standards in Environmental Chemistry and Biochemical Applications

Abstract

We have recently synthesized a series of monofluorinated polycyclic aromatic hydrocarbons (F-PAHs) and found that they provide a promising set of internal standards for environmental analysis of trace-level PAHs. Fluorine substitution has two antagonistic effects: the creation of a permanent dipole moment and the reduction of the London forces. As a result, F-PAHs are largely similar to the corresponding non-fluorinated PAHs in terms of physico-chemical properties. PAHs are routinely determined in many types of samples because of their carcinogenic properties, and in this chapter we address the suitability of F-PAHs as internal standards in PAH analysis during sample preparation, for liquid and gas chromatography, and for Shpol'skii spectroscopy. Additional work indicates that F-PAHs are also useful as marker compounds in mechanistic studies. Because of the strength of the fluorine-carbon bond, fluorine substitution can be used to block certain positions of the hydrocarbons, and the bond is highly resistant to scrambling.As illustrations, fluoropyrene metabolism in vivo and flash vacuum thermolysis are discussed.