EAGER: Dimerization of Heterotriquinacenes to Heterododecahedranes

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In this project, funded by the Chemical Synthesis Program of the Division of Chemistry, Professor Mark Mascal of the Department of Chemistry at the University of California Davis is exploring the production of new molecules that have curved surfaces. The approach involves the use of light to join two bowl-shaped molecules into products that are in the shape of a dodecahedron, one of the Platonic solids. This research has the potential to change the way chemists approach the synthesis of spherical molecules, which can have far-reaching applications in other branches of science including applied material science and nanotechnology. Graduate students are involved as teaching assistants in a chemistry study-abroad program. The researchers participate in a University of California Professional Development Program and undergraduate researchers from underrepresented groups participate in hands-on research activities. The project consists of three separate approaches to effecting the photochemically-allowed dimerization of triquinacenes and/or heterotriquinacenes to dodecahedranes/heterododecahedranes. The first approach involves the use of aggregation effects on cycloaddition reactions in water suspensions, which can dramatically increase rates by exerting pressure on the components within aqueous cavities. A second approach is to pair a triquinacenium cation-based amphiphile with a water-soluble, anionic triquinacene and organize the cation at the air / water interface. Strong ion pairing and hydrophobic forces may bring the components together in the right orientation for dimerization. Finally, a crystal engineering approach is also being adopted which may induce triquinacenes to orient with concavities in sufficiently close contact to allow topochemical (solid state) dimerization. The broader impacts include training students in interdisciplinary research encompassing organic synthesis, photochemistry, theoretical chemistry, and nanotechnology. Student researchers from a broad representation of ethnicities are engaged at all levels in this project.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.