Formation of carbon-carbon bonds in the photochemical alkylation of polycyclic aromatic hydrocarbons.

Abstract

The reaction of polycyclic aromatic hydrocarbons (PAHs) with alkanes was examined in the presence of ultraviolet (UV) light under model prebiotic Earth and interstellar medium (ISM) conditions. We observed the formation of alkylated PAHs from a variety of PAHs and alkanes, which was caused by the absorption of UV light by the PAH molecule. Photoalkylation occurred in PAHs and alkanes in solution, in thin films in contact with simulated ocean water, and in matrices simulating ISM conditions. Photoalkylation occurred readily, with significant product yields within 5 h of irradiation. Because alkanes and PAHs are presumed to be part of the organic inventory in the ISM and on the early Earth, we propose that this photoalkylation reaction is a plausible pathway for the formation of carbon-carbon bonds in both these environments.