Exploring the Design and Synthesis of Conjugated Materials for Applications in Organic Electronics

Organic electronics offer a variety of advantages over traditional electronics, but their study is hindered by their difficult syntheses. Herein, I tackle several difficult targets of interest to the molecular electronics and organic photovoltaics disciplines, and in doing so I try to illuminate what is and isn’t possible with this frontier of molecular design. I explore the viability of highly sterically-hindered systems enforce intramolecular π-π stacking and tune the 3-dimensional packing of otherwise flat conjugated molecules. In general, these molecules face many of the solubility issues that face large conjugated systems, while now also facing difficult bond formation because of steric bulk. In the case of building small molecule electron acceptors for organic photovoltaics, the electron deficient nature of these compounds also appears to inhibit the formation of these constrained systems. Then, I explore the limits of divergent synthesis by attempting to incorporate two distinct divergent steps into the synthesis of an acceptor unit for photovoltaic polymers. This proved to be a challenging goal, and many issues with orthogonality and reactivity are addressed. Ultimately, the development of this synthesis remains in progress because of Then, I discuss the development of oligophenyl dithiols used for studying tunneling and other electron transport through self-assembled monolayers. These monolayers are a promising frontier in designing molecular electronics. First, our syntheses produce terphenyl and quaterphenyl dithiols for a length-dependent study of electron transport. Then, we design a synthesis of similar oligophenyl dithiols that have sterically hindered rotations so that we can study the effect of inter-ring conjugation on electron transport through the monolayer. I conclude by discussing the themes shared by each of these diverse projects in organic electronics and by touching on issues that remain in the field of organic electronics. Finally, I touch briefly on the culture of scientific publishing against which these projects have strived to be high impact and publishable.Doctor of Philosoph