Date of Award

1-1-2011

Document Type

Campus Access Dissertation

Department

Chemistry and Biochemistry

Sub-Department

Chemistry

First Advisor

Lavigne, John J

Abstract

Boronate-containing materials have been extensively investigated in the recent decade because these compounds combine the advantages of dynamic reversibility to afford error checking mechanisms during synthesis and enhanced stability compared to conventional supramolecular polymers. Herein, we report on the synthesis, characterization, computational and property studies of boronate diesters based on fluorene boronic acid. These compounds exhibited tunable electronic properties with the incorporation of different substituents and linkages, therefore serving as excellent candidates for emissive materials. Meanwhile, computational studies were conducted to explain current experimental results and help focus future research directions. Though stability of these materials in aqueous environments remains a concern, a computational study demonstrated how the incorporation alkyl chains stabilized the boronate esters when exposed to water. Metallic elements were also introduced into these boronate systems increasing the potential for future research on these compounds as optical materials and semiconductors. Another project which grew from efforts at controlling the electronic properties of boronates identified a terephthalic acid derivative as a novel pH indicator. The intensity and wavelength of both absorption and emission changed as the pH changed providing a sensitive ratiometric probe.

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