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 10⁻¹-10⁻³ ohm⁻¹cm⁻¹. 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'-(3,3'-Dimethyl-4,4'-biphenylenebisazo) bisphenol 7, 4,4'-[azobis(p-phenyleneazo)] bisphenol 8, and 4,4'-(2-methoxy-1,4-phenylenebisazo) bisphenol 10 displayed liquid crystal (l.c.) properties, while model derivatives of 7, 8, and 4,4'-(4,4'-stilbenebisazo) bisphenol 9 did likewise. Monomers and derivatives of 4-[(4-hydroxyphenyl)azo]-1-naphthol 5, and 4,4'- [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 10⁻⁴ to 10⁻⁵ ohm⁻¹cm⁻¹. 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.
| Identifer | oai:union.ndltd.org:arizona.edu/oai:arizona.openrepository.com:10150/184215 |
| Date | January 1987 |
| Creators | KUO, THAU-MING. |
| Contributors | Hall, H. K. |
| Publisher | The University of Arizona. |
| Source Sets | University of Arizona |
| Language | English |
| Detected Language | English |
| Type | text, Dissertation-Reproduction (electronic) |
| Rights | Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author. |
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