Convex Polycycles: Synthesis, Structure, and Chemistry of Heterotriquinanes

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With the support of the Chemical Synthesis Program in the Division of Chemistry, Professor Mark Mascal of the University of California-Davis is studying molecules that have defined curvature, in particular a class of substances called "heterotriquinanes" which are bowl-shaped. This curvature can be increased until the molecules become spherical and such systems are also a subject of investigations. Molecules with the properties of interest allow the limits of chemical bonding theory to be tested and they also provide unique building blocks for the production of materials with novel properties of potential utility to science, engineering, and commerce. The broader impacts of the funded project extend to the benefits accrued to society as Professor Mascal and his coworkers engage in a range of K-12 outreach activities and the promotion of undergraduate research, particularly via programs that increase the participation of individuals belonging to underrepresented groups. Coworkers on the project will have the opportunity to serve as teaching assistants on a scientific and cultural study abroad program.The funded research revolves around conformationally rigid polyquinane heterocycles that range from gently curved (heterotriquinanes) to spherical (heterododecahedranes). The chemistry of these polycyclic ring systems proves to be uncommon and multifaceted, enabling synthetic objectives that embody extraordinary species with properties at the limits of canonical chemical bonding and structural theory, including unheard-of models of hypervalency (e.g., tetravalent oxygen), unknown zwitterionic species (e.g., stable oxygen ylides), and novel, non-planar aromatic ring systems (e.g., heteroacepentalenes). These projects will both advance fundamental science and provide new building blocks for advanced materials. The activities carried out under this award will also provide excellent opportunities for the participation of undergraduate students belonging to underrepresented groups through multiple programs at UC-Davis specifically established for such outreach, as well as the development of new educational materials that incorporate aspects of the research.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.