Excellence in Research- Dimeric Bis-Naphthoquinone Formation via a Green and Straightforward Approach Mechanistic and Adaptability Studies

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In this Excellence in Research project, Jayalakshmi Sridhar and Kevin Riley of the Department of Chemistry at Xavier University of Louisiana (XULA) explore the versatility of a newly discovered synthetic method for creation of dimeric quinone molecules with interesting properties. The goal of this research is to standardize the straightforward method for creation of designed dimeric quinones, which have strong potential in efficient energy storage systems (e.g. redox flow batteries), as coloring agents (dyes) and in pharmaceutical applications (e.g. therapeutics for diseases such as cancer and pathogenic infections). The project lies at the interface of organic, computational, materials and medicinal chemistry. Therefore, the project is well suited to train undergraduate students in multiple areas of chemistry. The collaborative research groups are well experienced in training undergraduate minority students in organic synthetic techniques and computational chemistry tools. The research groups are well positioned to provide the highest level of research training for students underrepresented in science and ensure their success in graduate schools. The students receive training in scientific explorations in chemistry labs, communication of results in oral and written formats at national conferences and enhancement of soft skills essential for succeeding in a scientific career. Homo- and heterodimeric quinones belong to an important class of molecules that have multiple applications in the areas of energy storage, pharmaceuticals and dyes. Dimeric quinones are capable of chelating to multiple metal cations with enhanced performance in redox flow batteries. These extended conjugated systems display pH-based color spectra. The quinone core moiety, found in several biologically active natural products, is amenable to modifications for targeting specific biomolecules. The newly identified synthetic method begins with Diels-Alder products undergoing redox reactions and Michael addition to form dimeric quinones. This reaction will be explored for its use in providing a predictable and easily adaptable way to create a wide array of homo- and hetero-bisquinone dimers. In this project, the following aspects of the new synthetic method are targeted for study. (1) The mechanism of the reaction will be studied using computational and synthetic methods with the goal of developing synthetic protocols into designed quinone dimers with specific structural features. (2) With the mechanistic insight gained, the team will explore the synthesis of homodimers with varied structural features including heterocyclic scaffolds; and (3) Similarly, the collaborative Sridhar/Riley team will examine the versatility of the reaction for the synthesis of heterodimers that are designed for specific end uses.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.