Real-World Applications of the Antiaromaticity Concept: Assemblies, Synthetic Strategies, and Functional Properties

University Of Houston, Houston TX

Investigators

Abstract

With the support of the Macromolecular, Supramolecular and Nanochemistry (MSN) Program in the Division of Chemistry, Judy Wu and her team at the University of Houston will carry out computational quantum chemistry research to explore, test, and validate molecular level design principles for functional carbon-rich materials, such as light-responsive polymers, nanotubes, and organic electronics. The expected outcomes include the development of practical guidelines that will complement current experimental interests and efforts, 1) to prepare smart polymers that can change shape or chemical properties when irradiated by light, 2) to grow carbon nanotubes with tailored dimensions and properties for energy storage and battery applications, 3) to design organic molecules with superior charge transport properties for transistors and bendable electronic devices, and overall, to speed up the discovery of functional molecules and materials by providing new and useful computational insight. Dr. Wu also co-leads and coordinates a monthly Theoretical Physical Organic Chemistry (TPOC) meeting. These meetings make high-quality scientific discussions accessible to graduate students and postdocs that are underrepresented in traditional in-person conferences, due to limitations in funding, resource, geographic location, or family conditions. These meetings also provide a safe place for students and postdocs in computational organic chemistry groups around the world to share their research with each other and to establish friendships that are beneficial for their career development. Specifically, the proposed research will stimulate chemist to reconsider practical applications of the concept of antiaromaticity in many areas of chemical research. Aim 1 investigates the potential of excited-state double proton transfer as a design strategy for photo-responsive hydrogen bonding motifs. Aim 2 set out to test the possibility of a metal-free, stepwise [4+2] cycloaddition, photochemical pathway for growing single-chirality nanotubes. Aim 3 seeks to establish a structure-property relationship to explain the effects of heteroatom doping and π-ring fusion on the electronic properties of polycyclic antiaromatic hydrocarbons. The proposed research will examine the possible role of antiaromaticity for designing light-responsive supramolecular systems, for developing synthetic strategies to access useful carbon-rich materials, and for tuning the optoelectronic properties of expanded π-conjugated materials. 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.