As a part of the Hartley research lab, this organic chemistry project is focused on the synthesis and structural study of pyrazine foldamers. Foldamers, which are a class of compounds that fold into an ordered state in solution, can mimic the geometries of nucleic acids and proteins. The goal of the project was to determine whether the oligo-pyrazine hexamer exhibits condensed or elongated folding behavior. The synthetic pathway involved repeated Suzuki and Stille coupling reactions, which were performed under argon atmosphere. Purification techniques such as column chromatography and liquid-liquid extraction were used extensively. Additionally, spectroscopic techniques like nuclear magnetic resonance spectroscopy and infrared spectroscopy were used to identify samples. The oligo-pyrazine trimer was quickly synthesized, however the next step to produce the tetramer has proven difficult with many tested reaction types and conditions producing no product. Current work is on testing new leaving groups and finding more suitable reaction conditions. If oligo-pyrazines exhibit elongated folding behavior sequences of oligo-pyrazines could be combined with sequences of o-phenylene foldamers, which exhibit a condensed folding structure, to create more interesting geometries. This discovery could potentially lead to the development of synthetic biological materials. This project has helped the student develop their lab skills as a synthetic organic chemist and has improved problem solving and scientific writing skills. These skills are especially helpful to a student entering graduate studies in chemistry.
Authors: Sean Ginn, Govinda Devkota, Yinhui Liao, and Dr. Scott Hartley
Advisor: Scott Hartley, Chemistry
Graduate Advisor: Govinda Devkota
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