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Synthesis of Alkyl Substituted Phenylated Poly(Ether Ether Ketone Ketone)s

Cerone, Matthew
http://rave.ohiolink.edu/etdc/view?acc_num=wright1496856789109456

Abstract Details

2017, Master of Science (MS), Wright State University, Chemistry.
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.
William Feld, Ph.D. (Advisor)
Eric Fossum, Ph.D. (Committee Member)
Ken Turnbull, Ph.D. (Committee Member)
80 p.
Chemistry; Organic Chemistry; Polymer Chemistry; Polymers
chemistry; organic chemistry; polymer chemistry; polymers

Recommended Citations

Citations

  • Cerone, M. (2017). Synthesis of Alkyl Substituted Phenylated Poly(Ether Ether Ketone Ketone)s [Master's thesis, Wright State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=wright1496856789109456

    APA Style (7th edition)

  • Cerone, Matthew. Synthesis of Alkyl Substituted Phenylated Poly(Ether Ether Ketone Ketone)s. 2017. Wright State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=wright1496856789109456.

    MLA Style (8th edition)

  • Cerone, Matthew. "Synthesis of Alkyl Substituted Phenylated Poly(Ether Ether Ketone Ketone)s." Master's thesis, Wright State University, 2017. http://rave.ohiolink.edu/etdc/view?acc_num=wright1496856789109456

    Chicago Manual of Style (17th edition)

wright1496856789109456
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This open access ETD is published by Wright State University and OhioLINK.