Date of Award

Fall 12-2014

Degree Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry and Biochemistry

School

Mathematics and Natural Sciences

Committee Chair

Karl J. Wallace

Committee Chair Department

Chemistry and Biochemistry

Committee Member 2

Song Guo

Committee Member 2 Department

Chemistry and Biochemistry

Committee Member 3

Douglas Masterson

Committee Member 3 Department

Chemistry and Biochemistry

Committee Member 4

Wujian Miao

Committee Member 4 Department

Chemistry and Biochemistry

Committee Member 5

Vijay Rangachari

Committee Member 5 Department

Chemistry and Biochemistry

Abstract

A coupling reaction has been used to successfully synthesize two novel probes utilizing coumarin derivatives as fluorophores. The structure, spectroscopy, and thermodynamics of these probes were characterized and studied. These probes, along with a classical probe using a N-methyl-anthranilate fluorophore, are used to take advantage of the ability of siderophores to coordinate Fe3+ ions which is coupled with the attractive phosphorescence properties of lanthanide ions. The use of lanthanide metals to create an indicator displacement assays is a novel application of these probes for the detection of Fe3+ ions. The use of Tb3+ ions as the indicator with a coumarin-based fluorophore showed the best detection which was both selective for the Fe3+ ion over other metal ions and showed the ability to detect the Fe3+ ion in water in concentrations as low as 3.9 μM. The work described with DFB also includes the thermodynamics for the DFB-iron complex in the gas-phase using ESI-MS. These ESI-MS techniques were applied to studying the fragmentation of a tripodal ligand with urea binding moieties that showed the ability to cyclize when fragmented. The fragmentation was found to cease due to a templating effect brought from an anion coordinated by the urea moieties of the probe.

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