CAREER: Convex Polycycles - Synthesis in the Azatriquinane Series

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This research program targets the synthesis of heteroatom-containing convex polycycles. A synthetic procedure for the alpha-substitution of azatriquinanes will be developed, and the properties and applications of resultant chiral azatriquinane-based acids, nucleophiles, and ligands will be investigated. Novel, fused tricyclic 10-pi aromatic systems derived from azatriquinacenes will be prepared and analyzed. Solid-state dimerization of azatriquinacene derivatives will yield diazadodecahedranes. These syntheses will be complemented by total syntheses of heterododecahedranes and advanced fragments thereof and of B- and P-heterotriquinane systems. These studies provide students with broad experience in organic synthesis, coordination chemistry, crystallography, and issues in chirality, aromaticity, and nanotechnology.With the support of this CAREER award from the Organic and Macromolecular Chemistry Program, Professor Mark Mascal, of the Department of Chemistry at the University of California at Davis, is exploring the synthesis and properties of molecules that envelop a volume of space, whether concave, hemispherical, or completely closed-shell bodies. Such molecules, perhaps most widely recognizable as the "fullerenes" ("Bucky balls"), represent both objects of enduring fascination in the chemical sciences and materials with potentially broad technological applications. This project serves as an excellent training ground for students in fundamental research. The project also targets a number of other developments regarding recruitment and training in the chemical sciences through enhancing the research relevance of laboratory courses, developing a modern industrial chemistry graduate course, promoting undergraduate research, and devising novel approaches to course assessment by student participation in the examining process, as well as providing popular outreach to regional community colleges and K-12 institutions.