Fluorescent Anion Sensors Based on the 2,6-bis-(2-Anilinoethynyl) Pyridine Scaffold
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The detection of anions has received considerable attention over the past twenty years due to their fundamental roles in biology and in our environment. The ability to sense these anions allows one the ability to study the basic science behind anion location and transport which is essential to understanding how cells, tissues, organisms, and ecosystems function. More importantly these sensors could be used to study a system where homeostasis has been disrupted. These sensors could prove to be valuable tools for studying disease processes and pollution detection. In order for these sensors to be practical they must have an easy to read output such as a color change, a change in fluorescence, or a change in electronic behavior. Furthermore, most biological systems and environmental systems of interest are in aqueous environments so having a sensor capable of functioning in water is a priority. Before any of these aspirations can be achieved a parent system must first be studied and refined, especially if one hopes to design a sensor capable of out-competing the hydration sphere that stabilizes most anions. Chapter I discusses traditional sensors for the detection of chloride. Specifically it will cover fluorophores that detect chloride. Chapter II focuses on preliminary work towards the development of water-soluble arylethynylpyridine fluorophores for the detection of anions. Chapter III further examines this class of arylethynylpyridine fluorophores and focuses on tuning optoelectronic properties. Chapter IV looks at the solid state morphologies and solvent tunability of arylethynylpyridine fluorophores. Chapter V explores one particular arylethynylpyridine fluorophores which forms nano-fibers in the presence of suitable anions. Chapter VI culminates in the development of water soluble fluorescent sensors for the detection of anions. Chapter VII concludes with the synthesis and study of a macrocyclic arylethynylpyridine fluorophore which was used to study the mechanism of fluorescence for this class of compounds. This dissertation contains my previously published and co-authored work.