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

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 center dot center dot center dot pi interactions, as indicated by analysis of crystal structures and Hirschfeld surfaces.

Automated summary

9,9 '-bianthryl and 9,9 '-biphenanthryl were synthesized by direct oxidative C-C coupling using divalent silver sulfate Ag(II)SO4 at ambient temperature conditions. Despite low yields of 6-10%, they present a competitive advantage compared to more complex synthetic pathways due to their single-pot process and lower waste generation. X-ray structures of adducts revealed that the aromatic hydrocarbon guest molecules were accommodated in cavities formed by the host 9,9 '-bianthryl molecule, primarily stabilized by C-H···π interactions.