Development of fluorescent sensors for the detection of hydrophobic amines and glycolipids

Field of study: Chemistry.Dr. Timothy E. Glass, Dissertation Supervisor.Includes vita."December 2017."A novel fluorescent sensor was designed and synthesized to detect hydrophobic amines and was used to extract them from synthetically prepared vesicles. This sensor had a higher affinity for diamines than primary amines, providing a fluorescence decrease upon binding both analytes. This sensor bound longer chain amines such as decylamine and 1,10-diaminodecane, better than shorter chain amines such as octylamine. This binding is influenced by both hydrophobic effects and electrostatic interactions between the sensor and analyte, driven by the hydrophobic cavity on the sensor. The sensor also unexpectedly binds to spermine and spermidine, however, with an increase in fluorescence. The mechanism for this phenomenon is not yet understood. The sensor showed it is possible to remove hydrophobic amines from synthetic veiscles, which can be applied to biological systems. A fluorescent sensor for glycolipids was also attempted to be synthesized by several different methods, incurring a new synthesis through redesigning the synthesis. Each method provided undesired products, decomposition, or no reactivity. Initial redesigns were due to complications in solubility of the carbazole aldehyde. Elongating the ester chain enhanced the solubility, but it remained unreactive towards any of the attempted reactions. This redesigned the sensor with a protected acid group that has been tested towards amide bond formation reactions to install the boronic acid or a haloarene, which will then undergo a Miyaura Borylation to install the boronic acid. If this does not prove successful, it will require alternative synthetic methods to install the boronic acid.Includes bibliographical references (pages 143-153)