Research in Prof. Funk’s lab continued to focus on two main projects: synthesis and catalytic applications of (cyclopentadienone)iron carbonyl compounds, and the development of a library of cyanuric chloride-based lipids for use in vaccine development and drug delivery—a collaboration with University of Kentucky College of Pharmacy Professor Vince Venditto (’03 Chem). Work on the latter project was carried out throughout the 2022 – 2023 academic year by Emily Howe (’23 BMB), Tommy Megna (’23 BMB), and Emily Sullivan (’24 BMB/Spanish).
We put on hold the synthesis of triazine-based lipids bearing esters—processes developed by Tommy and Emily Sullivan during the summer of 2022—and focused on developing an efficient synthetic approach to lipids with varying ionizable headgroups and hydrophobic tails of different lengths. Tommy’s and Emily Howe’s senior theses described their progress, and Prof. Funk and Emily Sullivan will use their routes to prepare a small library of lipids during the upcoming year. Prof. Funk plans to visit Prof. Venditto’s lab this year to prepare lipid nanoparticles, study their physical properties, and examine their transfection efficiencies.
Bryn Werley (’23 Chem/Music) continued her work on the (cyclopentadienone)iron carbonyl catalysis project. Most of her focus during her first-year through her junior year was on mechanistic studies, but with that work completed she turned her attention to oxidizing alcohols using biomass-based furfural as the terminal oxidant. Melanie Hempel (’20 BMB) started this project in 2018, and we are nearing the end of it after Cole Springer (’25 Chem/German Studies) identified and solved our product isolation problems last summer. Bryn continued Cole’s work exploring the reaction’s substrate scope and obtaining isolated yields of products. Sneha Jayaram (’25 Chem) joined the group in the spring 2023 semester, and she and Cole completed the project during the summer of 2023. Time to write the manuscript! Sneha also started a side project to see if we could use our catalysts to sustainably reduce bisulfite adducts of aldehydes, which are commonly used industrially to isolate unstable aldehydes. She got an exciting lead at the end of the summer she plans to pursue during the current academic year.
Prof. Funk gave an oral presentation at the Indianapolis ACS Meeting in March 2023 titled, “(Cyclopentadienone)iron carbonyl-catalyzed alcohol oxidations using furfural as a terminal oxidant.” Tommy Megna (’23 BMB), Emily Sullivan (’24 BMB/Spanish), Nicole Elahian (’24 Chem), and Cole Springer (’25 Chem/German Studies) all presented posters at the X-SIG poster session during Family Weekend in late October 2022. Also in October, Bryn Werley (’23 Chem/Music) gave an invited oral presentation titled “Isolation, characterization, and reactivity of a trimethylamine-ligated (cyclopentadienone)iron carbonyl compound” at the Gulf Coast Undergraduate Research Symposium at Rice University, winning first prize for her talk!
Four students in the Funk lab presented two posters at the Indianapolis ACS Meeting in March 2023. Bryn and Cole co-presented “Sustainable, iron-catalyzed alcohol oxidations with a biomass-derived terminal oxidant,” and Tommy and Emily Howe (’23 BMB) co-presented “Toward the synthesis of a library of triazine-based, biodegradable, cationic lipids.”
