LEAPS-MPS:Molecular Design, Synthesis, Properties, and Application of 2,5-bis(2-(4-nitrophenyl)ethynyl)thiophene Photolabile Protecting Groups for the Synthesis of Hydroxamic Acids

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This award is funded in whole or in part under the American Rescue Plan Act of 2021 (Public Law 117-2). In this project, funded by the Mathematical and Physical Sciences Directorate and the Chemistry Division, Professor Carl Saint-Louis and his students at Kennesaw State University (KSU) will study improved methods for synthesizing hydroxamic acids (HAs). HAs are chemicals that are utilized in many potential medical applications, including synthesis of drugs used in the treatment of cancer. In the organic synthesis field, HAs are utilized as precursors for a broad range of carbon-based chemical reactions, and as agents designed to bind to different metals. Synthesis and purification of HAs is challenging. Prof. Saint-Louis’s research will improve the synthesis of HA by eliminating the use of harsh and toxic conditions during the reactions and will facilitate purification of resulting HAs by reducing the by-products formed. Prof. Saint-Louis also plans to broaden participation in chemistry by students underrepresented in STEM fields by developing a strong undergraduate research program in his lab, and by building a mentoring group for underrepresented minority students on the KSU campus. He will not only leverage his own experiences to help support this large group of URM students, but will also bring URM scientists from off campus as speakers and role models. Professor Saint-Louis proposes to develop 2,5-bis(2-(4-nitrophenyl)ethynyl)thiophene (BNPET) photolabile protective groups (PPGs) with a diagnostic fluorescent by-product that would be utilized to quantify the amount of hydroxamic acid (HA) product formed. It has been shown that a major limitation of most o-nitrobenzyl (o-NB) PPGs derivatives is that their chromophores absorb light mostly in the UV region of the spectrum where extended exposure of cells or tissues to UV light can lead to cell damage or death. Proposed work will pave the way for the synthesis of various conjugated PPGs that absorb in the visible region of the spectrum for efficiency in biological applications. Prof. Saint-Louis will work to provide an improved understanding of the electronic properties of conjugated o-NB PPGs. Results from the planned work will have broad scientific impact by facilitating development of a new method to synthesize highly functional biologically relevant HA via a photo-cleavable protecting group. Work will be performed primarily by undergraduate students, and Prof. Saint-Louis will involve a large number of URM students directly in the planned research, in addition to serving as a mentor and role model to URM students campus-wide.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.