The Development of Dipyrrin Platforms for Oxygen Reduction

Myles Steed ’23

Student: Myles Steed ’23
Research Mentor: Allen Pistner (OWU Department of Chemistry)

Burning fossil fuels has caused great environmental health concerns. Constructing new green energy alternatives are vital to creating a better environment. My research has involved making a chemical that improves the usage of hydrogen fuel cells, one of the most promising green energy alternatives that is on the market today. It works by assisting in the chemical reaction of converting oxygen in the atmosphere into water, a necessary process in hydrogen fuel cell functioning.

A redox-active ligand scaffold, dipyrrin, was synthesized in the interest of activating oxygen. The synthesis of the scaffold was modified from previous pathways. The original pathway used a Negishi-coupling followed by condensation with a benzaldehyde using pyrrole and di-tert-butyl anisole before being demethylated using either boron tribromide or a thiolate. The modified synthesis constructs the scaffold with a Negishi-coupling followed by a condensation with a benzaldehyde using pyrrole and a silyl protected di-methyl-phenol before being deprotected using triethylamine trihydrofluoride. The new pathway provides the opportunity limit toxic reagents and improve the overall efficiency of the synthesis. The dipyrrin scaffold was synthesized with differing phenol and naphthol groups and was analyzed using UV-vis spectroscopy and electrochemistry. These compounds display a strong long-wave absorption and reversible redox activity, making these promising candidates to support catalytic activity. Attempts in the formation of metal complexes are currently underway.