CONVEX POLYCYCLES: SYNTHESIS, STRUCTURE, AND CHEMISTRY OF HETEROTRIQUINANES

University Of California-Davis, Davis CA

Investigators

Abstract

In this project funded by the Chemical Synthesis Program of the NSF Chemistry Division, Professor Mark Mascal of the Department of Chemistry at the University of California Davis is exploring fundamental aspects of molecular curvature and electronics. This project has the potential to substantially contribute to applied material science because of the relevance of 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 organic synthesis, noncovalent bonding, coordination chemistry, reactive intermediates, hypervalency, aromaticity, crystallography, theoretical chemistry, and 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 NSF Research Experiences for Undergraduates program, ACS Project SEED, the UC Davis Youth Scholars Program, and the UC COSMOS program. The project involves 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, which comprises three rings fused together in a rigid, puckered arrangement. Key features of synthetic interest are the oxidation of heterotriquinanes to bowl-shaped aromatic hemi-fullerene fragments, and the prospect of building up such structures into spherical heterododecahedranes. The triquinane platform also stabilizes chemical species that are normally seen only as reactive intermediates, such as tertiary oxonium salts, oxonium ylides, and even tetravalent oxadionium ions.