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

Jianping Lu, Kenji Miyatake, Antisar R. Hlil, Allan S. Hay

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

Three 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 difiuorides 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.

Original languageEnglish
Pages (from-to)5860-5867
Number of pages8
JournalMacromolecules
Volume34
Issue number17
DOIs
Publication statusPublished - 2001 Aug 14
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Fingerprint Dive into the research topics of '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'. Together they form a unique fingerprint.

  • Cite this