Date of Award

2019

Degree Type

Dissertation

Degree Name

Doctor of Philosophy in Chemistry

Specialization

Organic Chemistry

Department

Chemistry

First Advisor

Brenton DeBoef

Abstract

The main aim of this dissertation was to design and synthesize molecular probes with ease to be used in medical and environmental applications. The first chapter focuses on a novel pseudo-rotaxane probe that can be used in 129Xe imaging, which was synthesized using commercially available cyclodextrin moieties with a one-step reaction. This is probe can be synthesized in high yields and results in an acceptable level of hyperCEST depletion percentage. The second chapter showcases pillararenes as a potential candidate for 129Xe imaging. In addition, this chapter discusses the aid of a computational programs to design the supramolecular scaffold before the synthesis. The third chapter is an extension of the first chapter, which focuses on designing rotaxanes probes, which are interlocked molecular structures. Furthermore, these novel cyclodextrin based rotaxanes were able to capture a positively charged guest which gives an access point to use these as a potential drug delivery agent. Chapter 4 describes on a novel supramolecular scaffold that is synthesized using a co-pillararene. This fluorescent co-pillararene is capable of switching from a self-inclusion form to an open form via temperature, solvent and external guest, which makes this pillararene an excellent molecular switch. Chapters 5 and 6 elaborate the use of water-soluble pillararene structures in toxicant removal via host-guest inclusion phenomena and self-aggregation with the use of commercially existing double-stranded DNA. Chapter 7 deviates from the supramolecular regime and discusses the development of novel antibiotic drug molecules and their novel functionalization to increase their potency.

Available for download on Sunday, April 19, 2020

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