Development of Redox-Responsive Phenazine-Based Foldamers. Acylative Kinetic Resolution of Hydroxamic acids
Date of Award
Doctor of Philosophy (PhD)
Two different research directions have been presented in this thesis. The first project is about phenazine-based foldamers as molecular actuators. Researchers have been interested in the design and synthesis of foldamers and molecular actuators for years. We began our exploration by demonstrating that phenazine-1,6-dicarboxamides can function as redox-responsive molecular switches. We then designed and synthesized two generations of phenazine-based interleafed foldamers and studied their stability and redox behaviors under chemical and electrochemical conditions. In the second project, we have developed the first acylative kinetic resolution on hydroxamic acids. Although chiral hydroxamic acids have extensive applications, synthetic methods towards them are not straightforward. On the other hand, with easy access to racemic hydroxamic acids, kinetic resolution provides an attractive approach to enantiomerically enriched hydroxamic acids. We examined three class of substrates with our method and obtained synthetically useful selectivity factors.
Chair and Committee
Yin, Jingwei, "Development of Redox-Responsive Phenazine-Based Foldamers. Acylative Kinetic Resolution of Hydroxamic acids" (2022). Arts & Sciences Electronic Theses and Dissertations. 2787.