Synthesis of novel heterocyclic polymers via the chemistry of Reissert compounds

dc.contributor.authorGuilani, Bardiaen
dc.contributor.committeechairGibson, Harry W.en
dc.contributor.committeememberTanko, James M.en
dc.contributor.committeememberWard, Thomas C.en
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T21:33:43Zen
dc.date.adate2009-04-14en
dc.date.available2014-03-14T21:33:43Zen
dc.date.issued1990-01-15en
dc.date.rdate2009-04-14en
dc.date.sdate2009-04-14en
dc.description.abstractThe chemistry of a well established class of compounds, known as Reissert compounds, was used to prepare several novel N-heterocyclic polymers. Initially, alkylation of quinoline Reissert compounds was closely examined to test the feasibility of the use of such compounds as difunctional monomers. An A-B and an A-A monomer were then prepared by the reaction of quinoline with p-formylbenzoyl chloride and isophthaloyl chloride, respectively. The former monomer could be polymerized interfacially to afford a low molecular weight polyester exhibiting Tg of 190°C. Several novel bis-isoquinolines were prepared using an en amine reaction reported by Minter and Re.52 One of these bis-isoquinolines was used to prepare two novel bis-Reissert compounds which could be polymerized with several dialdehydes to obtain high molecular weight N-heterocyclic polyesters. Cleavage of the ester groups afforded a novel N-heterocyclic polyalcohol. It was observed that circumvention of a rearrangement reaction particular to Reissert compounds by molecular design led to the synthesis of N-heterocyclic polyesters that had the highest molecular weights and intrinsic viscosities. A novel N-heterocyclic difluorodiketone was prepared in four steps using the enamine reaction of Minter and Re52 and Reissert compound chemistry. The diketone was polymerized via standard techniques 72 to afford several novel poly(N-heteroaryl-ether-ketones) with high glass transition temperatures and thermal stabilities. Thus, polymerization of 1,4-bis(4-fluorobenzoyl)isoquinoline with biphenol yielded a poly(ether-ketone) with an intrinsic viscosity of 0.34 dl/g. This polymer showed Tg at 209°C and was stable up to 500°C in air.en
dc.description.degreeMaster of Scienceen
dc.format.extentx, 152 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-04142009-040537en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-04142009-040537/en
dc.identifier.urihttp://hdl.handle.net/10919/42072en
dc.language.isoenen
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V855_1990.G844.pdfen
dc.relation.isformatofOCLC# 21766551en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V855 1990.G844en
dc.subject.lcshHeterocyclic compounds -- Synthesisen
dc.subject.lcshPolymerizationen
dc.titleSynthesis of novel heterocyclic polymers via the chemistry of Reissert compoundsen
dc.typeThesisen
dc.type.dcmitypeTexten
thesis.degree.disciplineChemistryen
thesis.degree.grantorVirginia Polytechnic Institute and State Universityen
thesis.degree.levelmastersen
thesis.degree.nameMaster of Scienceen

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