Formation of Carbon-Carbon Bonds in the Photochemical Alkylation of Polycyclic Aromatic Hydrocarbons

The reaction of polycyclic aromatic hydrocarbons (PAHs) withalkanes was examined in the presence of ultraviolet (UV) lightunder model prebiotic Earth and interstellar medium (ISM)conditions. We observed the formation of alkylated PAHs from avariety of PAHs and alkanes, which was caused by the absorptionof UV light by the PAH molecule. Photoalkylation occurred inPAHs and alkanes in solution, in thin films in contact withsimulated ocean water, and in matrices simulating ISMconditions. Photoalkylation occurred readily, with significantproduct yields within 5 h of irradiation. Because alkanes andPAHs are presumed to be part of the organic inventory in the ISMand on the early Earth, we propose that this photoalkylation reactionis a plausible pathway for the formation of carbon-carbon bondsin both these environments.