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SYNTHESIS AND CHARACTERIZATION OF MONOMERS AND POLYMERS CONTAINING MULTIPLE P-ARYLENEAZO OR P-BENZOQUINODIIMINE GROUPS: CONDUCTING POLYMERS, LIQUID CRYSTAL POLYMERS, AND DIPOLAR POLYMERS

Posted on:1988-08-29Degree:Ph.DType:Dissertation
University:The University of ArizonaCandidate:KUO, THAU-MINGFull Text:PDF
GTID:1471390017956815Subject:Chemistry
Abstract/Summary:
Aniline Black, a polymer containing p-benzoquinodiimine groups, was synthesized chemically or electrochemically by the oxidation of aniline. The polymer salts showed the conductivity of 10{dollar}sp{lcub}-1{rcub}{dollar}-10{dollar}sp{lcub}-3{rcub}{dollar} ohm{dollar}sp{lcub}-1{rcub}{dollar}cm{dollar}sp{lcub}-1{rcub}{dollar}. Polymers containing anthroquinodiimine units were also prepared by polycondensations. The syntheses of model compounds containing p-benzoquinodiimine were attempted.; Multiazobisphenol monomers were synthesized. 4,4{dollar}spprime{dollar}-(3,3{dollar}spprime{dollar}-Dimethyl-4,4{dollar}spprime{dollar}-biphenylenebisazo) bisphenol 7, 4,4{dollar}spprime{dollar}- (azobis(p-phenyleneazo)) bisphenol 8, and 4,4{dollar}spprime{dollar}-(2-methoxy-1,4-phenylenebisazo) bisphenol 10 displayed liquid crystal (l.c.) properties, while model derivatives of 7, 8, and 4,4{dollar}spprime{dollar}-(4,4{dollar}spprime{dollar}-stilbenebisazo) bisphenol 9 did likewise. Monomers and derivatives of 4- ((4-hydroxyphenyl)azo) -1-naphthol 5, and 4,4{dollar}spprime{dollar}- (oxybis(p-phenyleneazo)) bisphenol 6 showed no l.c. behavior.; New thermotropic polyesters based on these multiazobisphenols were synthesized. Sebacates of 5, 6, 7, 8, and 10 showed l.c. behavior, while polymers based on isophthalic or 5-t-butylisophthalic acid did not do so. Polyformals were also synthesized from these momoners, only that of 4 showed weak l.c. behavior. The correlation between the structure of these polymers and their tractabilities, electrical properties, liquid crystal behaviors was studied.; Polymers and copolymers containing p-azoarylene and p-azoxyarylene groups were synthesized by oxidative coupling of various aromatic diamines. Films were cast directly from the reaction mixtures or from the polymer solution. The films were n-doped by sodium naphthalide or p-doped by iodine. They showed electrical conductivities of 10{dollar}sp{lcub}-4{rcub}{dollar} to 10{dollar}sp{lcub}-5{rcub}{dollar} ohm{dollar}sp{lcub}-1{rcub}{dollar}cm{dollar}sp{lcub}-1{rcub}{dollar}.; AB monomers containing dipolar p-phenyleneazo groups were synthesized: 4-(4-hydroxy-2-methoxyphenylazo) benzoic acid 21, 4- (4-(4-hydroxy-2-methoxyphenylazo)-2-methoxyphenylazo) benzoic acid 22, and 4-(4-hydroxy-2-methoxyphenylazo)-3-nitrobenzoic acid 23. The monomers were polymerized by direct polycondensations. The polyester synthesized from 21 formed a red, transparent film. A polymethacrylate containing dipolar p-phenyleneazo groups in the side chains was also prepared by the free radical polymerization of 1- (3-methoxy-4-(p-nitrophenylazo)-phenoxy) hexyl methacrylate 28.
Keywords/Search Tags:Containing, Polymer, Liquid crystal, P-benzoquinodiimine, Monomers, Synthesized, Dipolar, P-phenyleneazo
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