Chemistry of Strained Molecules with Radially Conjugated Pi Systems

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With the support of the Chemical Synthesis (SYN) program in the Division of Chemistry, Professor Ramesh Jasti of the University of Oregon (UO) is studying the synthesis, chemical reactivity, and properties of molecular fragments of carbon nanotubes. These macrocyclic synthetic targets are of fundamental interest for their structural, photophysical and electronic properties, and supramolecular chemistry, as well as their potential to lead to the uniform synthesis of carbon nanotubes. This research program, deeply rooted in organic synthesis and new synthetic methods, is also relevant to the fields of materials science, biology, and physics. The PI’s choice of challenging synthetic targets provides graduate and undergraduate students with a thorough background in synthetic organic strategy, methodology development, and reaction mechanism. In addition, these targets provide students opportunities to collaborate with physicists, engineers, and theorists to measure, utilize, and understand the physical properties of the newly created precision nanomaterials. Molecules with radially oriented pi-systems have been appreciated by chemists for decades, but have recently undergone a renaissance in that new developments in synthetic methodology have rendered what were previously mostly theoretical curiosities into now accessible structures. In this next grant period, the Jasti research group aims to continue to push the synthetic boundaries to the growing class of strained macrocycles with radially conjugated pi systems. Specifically, new pi-extended belt-like structures, twisted aromatics, and nitrogen doped nanohoops are all targeted in this grant cycle. In addition, strain promoted reactions of alkyne embedded nanohoops will be investigated as a rapid synthetic strategy to diversify this class of molecules. The methods and strategies developed for the targeted structures will be applicable to other types of polyaromatic hydrocarbons and new graphitic materials (not just the specific ones in this proposal) and therefore are of high intellectual merit. The PI also partners with the UO Summer Science program to provide educational experiences that highlight interdisciplinary research and hands-on science to groups of students that are traditionally underserved in the state of Oregon.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.