Unlocking Biologically-Relevant Opportunities Through Applications of Excited-State Aromaticity and Antiaromaticity

Project Summary A current research interest of my group is to develop conceptual models to explain, to understand, and to predict structure and reactivity in organic photochemistry. The premise is that Baird’s rule, i.e., the reversal of electron-counting rules for aromaticity and antiaromaticity in the ground and lowest excited-states of organic compounds, underlies many photochemical reactions essential to biology and biological applications. Some examples include light-induced bond twisting, photoheterolysis, electron transfer reactions, and proton-coupled electron transfer reactions. The innovation is that linking reactivity to the structural features of aromaticity and antiaromaticity may provide important chemical insights for designing new and useful reactions. Our research involves the use of a variety of computational quantum chemical tools, including time-dependent density functional theory (TD-DFT) and complete active space self-consistent field (CASSCF) methods. A five-year goal is to significantly demonstrate the usefulness of Baird’s rule in many areas of organic photochemistry. An overall vision of my research program is to prepare and foster a next generation of computational organic chemists and to translate theoretical insights into experimental opportunities for biological and biomedical research.