Methane gas is an integral component of Earth’s atmosphere, as it traps heat and allows our planet to retain a habitable temperature. However, the amount of atmospheric methane has increased by 70% due to human activity, such as cattle farming and fossil fuel production, contributing to an unsustainable heating of our planet. In nature, the metalloenzyme, soluble methane monooxygenase (sMMO), is used by bacteria to oxidize methane gas into liquid methanol. Drawing inspiration from the high-valent diiron active site of sMMO, we aimed to synthesize a homobimetallic complex supported by 3,6–diaminophenanthrene ligands, which we hypothesized would create a clamp-like pocket to capture methane due to C–H---π interactions between methane gas and the ligand, respecitvely. We propose that these interactions will donate electron density into methane’s σ* molecular orbitals, weakening its C–H bonds, and allowing oxidation to occur. We completed two five-step syntheses of novel 3,6–diaminophenanthrene pro-ligands with p–toludine and N,N–dimethylethylenediamine substituents. Amine substituents were installed in the final step by a palladium-catalyzed Buchwald-Hartwig amination reaction between the primary amines and 3,6–dibromophenanthrene. Pro-ligands and precursor compounds were characterized by 1H NMR and IR spectroscopy, and GCMS. We synthesized dicopper complexes of these ligands in preliminary reactions, and aim to target iron metalation reactions in the future.

Coordination of Cu(I) to 3,6–diamine phenanthrene ligands

Macromolecular Chemistry: The Second Century

[Author Benefits](https://scimeetings.acs.org/?utm_source=pubs_content_marketing&utm_medium=website&utm_campaign=0320_MCF_NPI_Launch_Spring_Homepage&ref=pubs_content_marketing)

[How to use SciMeetings](https://storage.googleapis.com/dl.morressier.com/acs/SciMeetings-ACSSpring2020-HowToGuide_M3020-Final.pdf)

[Frequently Asked Questions](https://storage.googleapis.com/dl.morressier.com/acs/SciMtng_ACSNMSp2020_FAQ_M3120_Final.pdf)

ACS Spring 2020 National Meeting & Expo

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