AN ELECTROANALYTICAL ASSESSMENT OF ORGANIC REDOX TRANSFORMATIONS IN BATTERY AND ELECTROSYNTHETIC APPLICATIONS

Abstract

Organic molecules are capable of diverse redox chemistries. This capability has traditionally been utilized by employing oxidizing and reducing agents in synthetic transformations. However, this method often requires the use of hazardous and environmentally harmful chemicals and is limited in terms of selectivity and applications. Electrochemical techniques enable a more precise control of these processes and can eliminate the need for these undesirable reagents. Further, these redox reactions can be utilized in a reversible manner for applications in energy storage devices. Herein, we employ electroanalytical techniques to explore the redox chemistry of organic materials in energy storage and electrosynthetic applications. We begin by reviewing the literature of high-power organic materials as battery electrodes to elucidate properties which enable high-rate capabilities. Based on our findings, we successfully developed a novel family of polymeric species sharing a diphenyl-phenazine redox-active moiety which exhibited impressive energy and power density capabilities as battery electrode materials. We proceeded to examine properties which enabled such high-performance through systematic studies of the impact of polymer structure and the interactions between redox-active species and charge compensating ions. In the final chapter, we apply electroanalytical techniques to organic reactions driven by electrochemical stimuli. With these methods, we examined the mechanisms of several electrochemically driven transformations and identified critical properties which determine reaction outcome. The mechanistic studies explored throughout this dissertation are intended to provide insight for future development and optimization of organic electrochemical systems.