Polycyclic Aromatic Hydrocarbons and their Adducts with Solvents from Ag(II)SO4-Based Oxidative C-C Coupling

Abstract

9,9′-bianthryl and 9,9′-biphenanthryl were synthesized by direct oxidative C–C coupling of anthracene and phenanthrene, respectively, using divalent silver sulfate Ag(II)SO4 under ambient temperature conditions. Syntheses proceed with rather low yields 6–10%, however, they are competitive to more complex synthetic pathways due to single-pot process and lower waste. The single crystal structures of 9,9′-bianthryl, 9,9′-biphenanthryl and adducts of 9,9′-bianthryl with benzene, toluene and o- and p-xylene were obtained. X-ray structure of the adducts attested that the guest molecules of aromatic hydrocarbons were accommodated in cavities formed by the host 9,9′-bianthryl molecule. The adducts are stabilized mostly by the C–H•••π interactions, as indicated by analysis of crystal structures and Hirschfeld surfaces.