Novel Soluble and Fluorescent Poly(arylene ether)s Containing p -Quaterphenyl, 2,5-Bis(4-phenylphenyl)oxadiazole, or 2,5-Bis(4-phenylphenyl)triazole Groups
2001; American Chemical Society; Volume: 34; Issue: 17 Linguagem: Inglês
10.1021/ma0103977
ISSN1520-5835
AutoresJianping Lu, Kenji Miyatake, Antisar R. Hlil, Allan S. Hay,
Tópico(s)Conducting polymers and applications
ResumoThree novel conjugated biphenols 3, 4, and 8 were synthesized by the Pd(OAc)2-catalyzed regioselective carbon−carbon coupling reaction of 2,6-di-tert-butylphenol or 2-phenylphenol with aryl halides. Although poly(arylene ether)s derived from biphenol 3 and arylene difluorides have low solubility in organic solvents, using 4,4'-(9-fluorenylidene)diphenol or 4,4'-(hexafluoroisopropylidene)diphenol as a comonomer gave soluble poly(arylene ether)s 6a−c. High molecular weight poly(arylene ether)s 7a'−c' were also prepared from biphenol 4. The biscarbamate-masked monomers 5 and 9 improved the polymerization to give higher molecular weight polymers 7a−e and 10a−e in higher yields. Polymers 7 and 10 possess better film-forming capabilities and are still soluble in organic solvents. Polymers 6, 7, and 10 are all thermally stable with 5% weight loss temperatures higher than 500 °C under nitrogen. The polymers show strong blue light emission ranging from 387 to 478 nm in solution, depending on the conjugated structure.
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