The spontaneous polymerization behavior of an acceptor substituted quinodimethane was investigated. High molecular weight homopolymers of 7,8,-di(ethoxycarbonyl)-7,8-dicyanoquinodimethane (DEDCQ) or copolymers of DEDCQ-styrene (St) and DEDCQ-p-methoxystyrene (p-MeOSt) were formed spontaneously in chloroform containing acetic acid. All polymerizations occurred by a radical mechanism. High molecular weight polymers formed at low conversion. Radical homopolymerization of DEDCQ was promoted by ambient light or heat. DEDCQ-p-MeOSt copolymerizations yielded alternating copolymers, which formed rapidly relative to the DEDCQ homopolymers and copolymers (rich in styrene). All of these polymerizations are thought to begin with a bond forming mechanism and propagate by polyaddition. A new acceptor group substituted quinodimethane was synthesized, characterized and copolymerized with electron donating monomers. Oxidation of the dianion of α, α'-dicyano-α, α'-diphenyl-p-xylene yielded 45% 7,8-dicyano-7,8-diphenylquinodimethane. In solution this compound exists in both the trans and cis forms but forms a sharply melting crystalline solid. It was resistant to homopolymerization but did form low molecular weight copolymers with electron rich aromatic monomers.
| Identifer | oai:union.ndltd.org:arizona.edu/oai:arizona.openrepository.com:10150/184341 |
| Date | January 1988 |
| Creators | Brandt, Martin William |
| Contributors | Mulvaney, J. E., Hall, H. K., Green, G. D. |
| 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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