Methane is a harmful greenhouse gas, emitted during the production of natural gas and biogases, but when converted to methanol finds application in antifreeze, gasoline and diesel fuel production, trans-esterification reactions and waste-water treatment. However, current commercial conversion of methane to methanol requires heat and high pressures. In nature, soluble methane monooxygenase (sMMO), an enzyme with a carboxylate-bridge diiron active site, facilitates the conversion of methane to methanol under mild temperature and pressure conditions. Drawing inspiration from the active site of sMMO, we aimed to synthesize a diiron complex of N,N-diphenylphenanthrene-3,6-diamine through a five-step synthesis, which included Buchwald-Hartwig Cross-Coupling Amination, Horner-Wadsworth-Emmons, and photocyclization reactions as key synthetic steps. N,N-diphenylphenanthrene-3,6-diamine was synthesized in 91% yield and characterized by 1H and 13C NMR, and IR spectroscopy, and precursor compounds were characterized by 1H NMR spectroscopy and GCMS. The pro-ligand was then deprotonated with n-butyllithium and reacted with copper(I) iodide. Preliminary results indicated that a dicopper complex was synthesized. Metalation reactions of our novel ligand with iron will be targeted in future work.

Synthesis and coordination of N,N-diphenylphenanthrene-3,6-diamine to metal cations

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.