CONVEX POLYCYCLES: SYNTHESIS, STRUCTURE, AND CHEMISTRY OF HETEROTRIQUINANES

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In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Mark Mascal of the Department of Chemistry at the University of California Davis will explore the fundamentals of molecular curvature and electronics by synthesizing organic polycycles that enclose volumes of space, from concave, to hemispherical, to completely closed shell bodies. The research program revolves around the triquinane molecular framework, a rigid, bowl-shaped, fused tricycle. Key features of synthetic interest are the oxidation of heterotriquinanes to nonplanar aromatic hemi-fullerene fragments, and the prospect of building out such structures into heterododecahedranes. The triquinane platform stabilizes chemical species that are normally seen only as reactive intermediates, such as tertiary oxonium salts, oxonium ylides, and tetravalent oxadionium ions. In addition to the fundamental scientific impact, this project has the potential to contribute substantially to applied material science, in view of the continuing interest in curved aromatic surfaces in the area of nanotechnology. The broader impacts in terms of training and diversity lie in the program's interdisciplinary nature, encompassing at various points organic synthesis, noncovalent bonding, coordination chemistry, reactive intermediates, hypervalency, issues in aromaticity, crystallography, theoretical chemistry, and aspects of nanotechnology. Principal educational deliverables are the incorporation of research into undergraduate chemistry laboratory courses and the promotion of undergraduate research, particularly involving under-represented groups, through the involvement in dedicated, university-sponsored programs. Outreach involves participation in the ACS Project SEED, the UC Davis Youth Scholars Program, and the UC COSMOS program.