Date of Award

2014

Degree Type

Thesis

Degree Name

Master of Science in Chemistry

Department

Chemistry

First Advisor

Brenton DeBoef

Abstract

The lack of resolution and selectivity in current imagining techniques such as x-ray, optical, and magnetic resonance imaging (MRI) has excelled the development of new biosensor technologies. Cryptophane A, a molecular cage composed of two cyclotriveratrylene (CTV) units connected by alkoxy bonds, can be turned into biosensors by attaching a target moiety capable of binding to a particular analyte. Cryptophanes can encapsulate xenon making it an attractive biosensor candidate for detection by hyperpolarized xenon-129 (HP-129Xe) MRI. Further detection enhancement is achieved by using a technique called hyperpolarized chemical exchange saturation transfer (HYPER-CEST). One of the key challenges in developing Xe-biosensors is the need for water soluble cryptophanes and their attachment to biomolecules that specifically bind physiological targets.

The first manuscript entitled “Functionalization of Cryptophane cages for Xenon MRI” discusses the synthesis of cryptophane cages and their potential to be further functionalized. The manuscript centers on synthesizing cryptophanes that are water soluble functionalized with gold nanoparticles, which can eventually be further modified for imaging molecular events in vivo.

The second manuscript, “Vanadium Catalyzed Oxidative Coupling of sp3 C-H Bonds to Heteroarenes” discusses oxidative aminomethyaltion of imdizolpyridines. This manuscript proposes a vanadium catalyzed oxidative coupling of imidazopyridines with N-methylmorpholine oxide which serves as both sp3 hybridized coupling partner and the oxidant. The reaction was optimized and performed with a variety of substrates to yield on a library of aminomethylated products. We investigated the mechanism and propose that a Mannich-type mechanism is responsible for the formation of the product.

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