Virginia Tech
Studies Toward Highly Fluorinated Polyphenylenes by Diels-Alder Polymerization
Abstract
dc:description.abstractDiels-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.
Degree
thesis:*- Name thesis:degree_name
- Master of Science
- Level thesis:degree_level
- masters
- Discipline thesis:degree_discipline
- Chemistry
- Department dc:contributor.department
- Chemistry
- Grantor dc:publisher
- Virginia Tech
- Year dc:date.issued
- 2008
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Sen, Sanghamitra
- Chair dc:contributor.committeechair
-
- Deck, Paul A.
- Committee members dc:contributor.committeemember
-
- Kingston, David G. I.
- Long, Timothy E.
- Madsen, Louis A.
- Turner, S. Richard
Subjects
dc:subject × 4Rights
dc:rights- Statement dc:rights
-
- In Copyright
- Licence dc:rights.uri
Identifiers
dc:identifier.*- Dc Identifier Other
- etd-05072008-112106
- OAI identifier oai:identifier
- oai:vtechworks.lib.vt.edu:10919/32320