Tautomerically Active Modules in Extended pi-Electron Systems

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In this project funded by the Macromolecular, Supramolecular and Nanochemistry Program of the Chemistry Division, Ronald K. Castellano of the University of Florida will synthesize and characterize pi-conjugated molecular systems containing tautomerically active heterocyclic building blocks that ultimately could be used to create materials with tunable physical, chemical, supramolecular, and optoelectronic properties. Experimental and theoretical studies will systematically explore the interplay between tautomerism and extended pi-electron delocalization in three settings: (1) fused polycyclic aromatic ring systems; (2) linear pi-conjugated architectures; (3) supramolecular aggregates. The broader impacts of the project include training graduate and undergraduate students in multidisciplinary science in preparation for their future careers. The students involved in the project will also participate, as graduate/undergraduate teams and together with the University of Florida Chemistry Club, in the delivery of standards-aligned experimental modules to science classrooms around Alachua County, Florida. Electrically conducting carbon-based (organic) molecules and polymers hold enormous promise for realizing highly efficient, affordable, and broadly available electronic and optical devices. This research explores a general approach to prepare "adjustable" versions of these materials with tunable or environmentally responsive properties. The results of the studies could facilitate access to high performing organic light-emitting devices, solar cells, and sensors.