Publication Date
2017
Document Type
Thesis
Committee Members
William Feld (Advisor), Eric Fossum (Committee Member), Ken Turnbull (Committee Member)
Degree Name
Master of Science (MS)
Abstract
A phenylated bis(fluorobenzoyl) monomer, 5-hexyl-2,3-diphenyl-1,4-bis(fluorobenzoyl)benzene, was synthesized via a four-step process. The first three compounds synthesized were diethyl 5-hexyl-2,3-diphenyl-1,4-benzenedicarboxylate, 5-hexyl-1,4-bis(hydroxymethyl)-2,3-diphenylbenzene and 5-hexyl-2,3-diphenyl-1,4-benzenedicarboxaldehyde. The final step involved the reaction of the Grignard formed from p-bromofluorobenzene with the dialdehyde to yield a diol intermediate which was oxidized to the bis(fluorobenzoyl) monomer by use of a Jones oxidation. The monomer was polymerized by nucleophilic aromatic substitution (NAS) with bisphenol-A, resorcinol, and hydroquinone in N-methyl-pyrrolidone (NMP) to yield novel, phenylated PEEKKs. The number-average molecular weights (Mn) for the polymers were found to be 35,700 g/mol, 34,800 g/mol and 28,000 g/mol, respectively and the weight-average molecular weights (Mn) for the polymers were found to be 63,000 g/mol, 85,100 g/mol and 55,600 g/mol, respectively with dispersities of 1.76, 2.44 and 1.98, respectively. Thermal analysis provided both the glass transition temperatures (Tg) of 164°, 148°, 162°, respectively and the 5% thermal decomposition temperatures (Td5%) of 460°, 448°, 458°, respectively. All of the polymers were highly soluble in chlorinated solvents and formed robust, free-standing, thin films.
Page Count
80
Department or Program
Department of Chemistry
Year Degree Awarded
2017
Copyright
Copyright 2017, all rights reserved. My ETD will be available under the "Fair Use" terms of copyright law.
