Publication Date


Document Type


Committee Members

William Feld (Advisor), Eric Fossum (Committee Member), Ken Turnbull (Committee Member)

Degree Name

Master of Science (MS)


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


Department or Program

Department of Chemistry

Year Degree Awarded


Included in

Chemistry Commons