Convex Polycycles: Synthesis, Structure, and Chemistry of Heterotriquinanes

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This research program is based around the synthesis and applications of heteroatom-containing, convex polycycles. The principal goals of the project are to prepare azatriquinanes which are asymmetric at the nitrogen atom for applications to chiral H+ or X+ delivery, to produce a range of azatriquinane-based transition metal ligands and host-guest systems, to synthesize new series of hetero (O, S, P, and/or B) triquinanes, triquinacenes, and acepentalenes, to devise a new synthetic entry into the heterotriquinane ring system via cyclononatrione, and to approach heterododecahedranes both by heterotriquinacene dimerizations and by total synthesis. These investigations will provide the researchers with broad experience in organic synthesis, coordination chemistry, crystallography, and fundamental aspects of aromaticity, strain, electron delocalization, and molecular architecture.With the support of this award from the Chemical Synthesis Program, Professor Mark Mascal of the Department of Chemistry at the University of California Davis will explore the nature of molecules with curved surfaces -- from concave, to hemispherical, to completely closed-shell, polyhedral bodies. The study of such molecules answers fundamental questions regarding the electronic structure of organic (carbon-based) materials, and also presents opportunities for practical applications, particularly in the area of nanotechnology. This project also serves as an excellent training ground for graduate and postdoctoral researchers in fundamental and applied chemical synthesis. The broader impacts of this program include K-12 outreach by sponsoring summer research projects via the American Chemical Society SEED and UC Davis Youth Scholar Programs, the development of innovative student learning and assessment practices, involvement in programs which promote the participation of underrepresented groups in the Pacific Rim, and enhancing the relevance of research chemistry in undergraduate laboratory courses. Finally, the visual impact and beautiful symmetry of the curved and spherical molecular bodies being studied lends itself to additional outreach opportunities through the popular press and public science venues, and thereby a greater appreciation of the art of technology.