Development of Phosphoryl-Bridged Viologens Toward Functional Materials
Abstract
The work in this thesis provides a new class of viologen-based materials, phosphoryl-bridged viologens, for applications in organic electronics. Each chapter focuses on the properties of the materials and their applicability to a specific application. In addition, the chapters build upon the synthesis and properties of each other leading to a better understanding of phosphoryl-bridged viologens and more sophisticated applications. Chapter Two utilized the beautiful electrochromic character of phosphoryl-bridged viologens for application in electrochromic devices. Successful functionalization with various benzyl-substituents led to modification of the reduction potential but preserved the colour of the species, leading to a proof-of-concept electrochromic device. Chapter Three built upon the synthesis from the previous chapter, expanding a library of monomer to a library including dimers and main-chain polymers with the phosphoryl-bridged viologen core. The materials discussed in this chapter resulted in hybrid organic/Li- ion battery half-cells with the potential application for fully organic batteries. While phosphoryl-bridged viologens are not the current front-runners in this field, they offer a unique property that allows for increased charge to mass ratios for a higher energy density material. In addition, the phosphoryl-bridged viologen utilized offer exceptionally charging/discharging stability, which is a current pitfall of Li-ion batteries. Chapter Four developed new functionalizations of phosphoryl-bridged viologens for anchoring onto inorganic nanoparticles or immobilized substrates increasing the utility of this family of materials. Phosphoryl-bridged viologens proved to be excellent electron-acceptors of photoexcited titanium dioxide electrons for potential applications in photocatalysis. In addition, this chapter features the stable methyl viologen and phosphoryl-bridged viologen radicals in water, where their brilliant colour is preserved over several hours. Finally this thesis concludes with an immediate outlook on these materials and their potential success in organic electronics. The goal of this thesis was to establish a new library of phosphoryl-bridged viologens and demonstrate preliminary applications as organic electronic materials.
Description
Keywords
Chemistry--Inorganic
Citation
Stolar, M. (2017). Development of Phosphoryl-Bridged Viologens Toward Functional Materials (Doctoral thesis, University of Calgary, Calgary, Canada). Retrieved from https://prism.ucalgary.ca. doi:10.11575/PRISM/25687