Title page for ETD etd-05072008-112106

Type of Document Master's Thesis
Author Sen, Sanghamitra
Author's Email Address sansen78@vt.edu
URN etd-05072008-112106
Title Studies Toward Highly Fluorinated Polyphenylenes by Diels-Alder Polymerization
Degree Master of Science
Department Chemistry
Advisory Committee
Advisor Name Title
Deck, Paul A. Committee Chair
Kingston, David G. I. Committee Member
Long, Timothy E. Committee Member
Madsen, Louis A. Committee Member
Turner, S. Richard Committee Member
  • Polyphenylenes
  • Diels-Alder Polymerization
  • Nucleophilic Substitution
  • Fluorine
Date of Defense 2008-04-28
Availability unrestricted
Diels-Alder polyphenylenes (DAPPs) are chemically and thermally stable polymers, used for dielectric resins, gas separation membranes, and fuel cell proton exchange membranes. Highly fluorinated DAPPs are expected to have better thermal stability and chemical resistance, higher glass transition temperatures, improved compatibility with other fluorinated polymers (like NafionTM), and better adhesion to certain surfaces such as some metals. This thesis proposes a synthesis of highly fluorinated DAPPs by reacting novel, fluorinated bis-cyclopentadienone (CPD) monomers with known aromatic dialkynes.

This thesis starts with an introduction to DAPP synthesis, properties, and applications. The second chapter focuses on the synthesis of 4,4’-bis[1,2,4-tris(perfluoro-4-tolyl)cyclopentadien-5-one-3-yl]octafluorobiphenyl (CPD monomer). In the first step, disodiumbis(cyclopentadieny)octafluorobiphenyl was combined with 6 equivalents of octafluorotoluene in HMPA to give 4,4’-bis[1,2,4-tris(perfluoro-4-tolyl)cyclopentadiene-3-yl]octafluorobiphenyl. Oxidation to the corresponding diketone was effected using selenium dioxide. The synthesis of CPD monomer presented several unexpected challenges that were ultimately overcome. The third chapter describes a series of initial polymerization experiments as well as some model reactions that were carried out to understand monomer reactivity. Finally the future research plan of synthesizing different polymers by Diels-Alder reaction and nucleophilic substitution reaction has been discussed.

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