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dc.contributor.advisorGlass, Timothy E. (Timothy Edward)eng
dc.contributor.authorLittlefield, Charles W., Jr.eng
dc.date.issued2017eng
dc.date.submitted2017 Falleng
dc.descriptionField of study: Chemistry.eng
dc.descriptionDr. Timothy E. Glass, Dissertation Supervisor.eng
dc.descriptionIncludes vita.eng
dc.description"December 2017."eng
dc.description.abstractA 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.eng
dc.description.bibrefIncludes bibliographical references (pages 143-153).eng
dc.format.extent1 online resource (xiv, 154 pages) : illustrations (some color)eng
dc.identifier.merlinb129183350eng
dc.identifier.oclc1098243397eng
dc.identifier.urihttps://hdl.handle.net/10355/63668
dc.identifier.urihttps://doi.org/10-32469/10355/63668eng
dc.languageEnglisheng
dc.publisherUniversity of Missouri--Columbiaeng
dc.relation.ispartofcommunityUniversity of Missouri-Columbia. Graduate School. Theses and Dissertationseng
dc.rightsOpenAccesseng
dc.rights.licenseThis work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License.eng
dc.titleDevelopment of fluorescent sensors for the detection of hydrophobic amines and glycolipidseng
dc.typeThesiseng
thesis.degree.disciplineChemistry (MU)eng
thesis.degree.grantorUniversity of Missouri--Columbiaeng
thesis.degree.levelDoctoraleng
thesis.degree.namePh. D.eng


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