Publication Date
2015
Document Type
Thesis
Committee Members
William Feld (Advisor), Eric Fossum (Committee Member), Daniel Ketcha (Committee Member)
Degree Name
Master of Science (MS)
Abstract
The synthesis of the NAS monomer, 4-fluoro-4'-(2-(4-benzyloxyphenoxy)ethoxy) benzophenone, was envisioned as a two-step process. Thus, the synthesis of 4-fluoro- 4'-(2-(4-benzyloxyphenoxy)ethoxy)benzophenone was accomplished by the reaction of 4-fluoro-4'-hydroxybenzophenone and 1-(benzyloxy)-4-(2bromoethoxy) benzene. Hydrogenation of 4-fluoro-4'-(2-(4-benzyloxyphenoxy)ethoxy) benzophenone with 10% Pd/C was used to successfully remove the benzylic ether protective group, however, the reaction also reduced the benzophenone carbonyl. The synthesis of the EAS monomer, 4-(2-(4-phenoxyphenoxy)ethoxy)benzoic acid, was also a two-step process. The reaction of ethyl p-(2-hydroxyethoxy)benzoate and 4-phenoxyphenol gave ethyl 4-(2-(4-phenoxyphenoxy)ethoxy)benzoate in good yield. This ester could be easily hydrolyzed to 4-(2-(4-pheonxyphenoxy)ethoxybenzoic acid. The polymerization of the EAS monomer, 4-(2-(4-pheonxyphenoxy)ethoxybenzoic acid, was carried out using Eaton's Reagent (methanesulfonic acid, phosphorous pentoxide). The polymer exhibits low solubility in common solvents, had an average inherent viscosity of 0.62 dL/g, exhibited DSC transitions from 100°-120° and showed a substantial weight loss in TGA around 400°.
Page Count
80
Department or Program
Department of Chemistry
Year Degree Awarded
2015
Copyright
Copyright 2015, all rights reserved. My ETD will be available under the "Fair Use" terms of copyright law.
