Live Poster Session: Zoom Link
Thursday, July 30th 1:15-2:30pm EDT
Abstract: Several research projects in the Northrop lab have focused on the synthesis and self-assembly of large molecular frameworks of different shapes and sizes that are able to function as semiconductive organic materials. While there has been some success at synthesizing semiconductive organic polymers and frameworks from boronic acids and catechol derivatives to form boronate ester frameworks, which were conjugated through boron’s empty p orbital, this study explores a possible new route using diamines and quinones to form a more conjugated framework of quinoxalines in which the structure is conjugated with π-bonds through the entire structure. Nine diamines and eight quinones and their 85 combinations of quinoxalines were studied computationally using Gaussian software to survey the impact of structure and functionality on the energetics of quinoxaline formation. Here we show the enthalpies and free energies of the quinoxalines calculated at the B3LYP-6/311G(d) and M06-2x/6-311G(2p,d) levels of theory, and are able to draw initial conclusions regarding the impact of withdrawing groups, donating groups, and constitutional isomerism on quinoxaline formation. The electronic properties of resulting quinoxalines were also investigated quantitatively by calculating their HOMO and LUMO gaps and qualitatively by plotting those molecular orbitals. We found that all of the quinoxaline formations were spontaneous (∆G° <0) and their HOMO-LUMO gaps ranged between 2.5 to 4 eV.
QuinoxalineProject2020-final-Corin-GradyLive Poster Session: Zoom Link
Thursday, July 30th 1:15-2:30pm EDT