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Date of Award

9-2013

Document Type

Campus Access

Degree Name

Doctor of Philosophy (PhD)

Degree Program

Chemistry

First Advisor

D. Venkataraman

Second Advisor

Scott M. Auerbach

Third Advisor

Nathan Schnarr

Subject Categories

Chemistry | Organic Chemistry

Abstract

This dissertation utilizes the power of organic synthesis to construct novel chiral and achiral π -conjugated organic molecules/materials that serve as platforms for single molecule chiroptical studies, to develop optical sensors and solar thermal fuels. The first section of the dissertation describes the synthetic methodologies employed to obtain chiral bridged triarylamine helicene scaffolds with well defined molecular orientation (relative to the surface) on a surface, to address the fundamental question: What is the role of molecular orientation on the magnitude of chiroptical response of a chiral molecule? Next, we investigated bridged triarylamine chromophores for optical sensing. We developed a novel bridged triarylamine helicene that shows turn-on sensory response towards toxic nerve agent mimics such as dichloroethylphosphate (DCP). The final section of this dissertation addresses the question: Can mechanical energy induce a change in configuration from cis-azobenzene to trans-azobenzene? For this purpose, we developed an azobenzene-functionalized polymer and showed that ultrasound-induced mechanical energy isomerizes the azobenzene moiety within the polymer fromcis to trans configuration without cleaving the azo bond.

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