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


Included in

Chemistry Commons

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