New poly(arylene ether)s with pendant phosphonic acid groups

Kenji Miyatake, Allan S. Hay*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

75 Citations (Scopus)


Soluble brominated poly(arylene ether)s containing mono- or dibromotetraphenylphenylene ether and octafluorobiphenylene units were synthesized. The polymers were high molecular weight (weight-average molecular weight = 115,100-191,300; number-average molecular weight = 32,300-34,000) and had high glass-transition temperatures (>279 °C) and decomposition temperatures (>472 °C). The brominated polymers were phosphonated with diethylphosphite by a palladium-catalyzed reaction. Quantitative phosphonation was possible when 50 mol % of a catalyst based on bromine was used. The diethylphosphonated polymers were dealkylated by a reaction with bromotrimethylsilane in carbon tetrachloride followed by hydrolysis with hydrochloric acid. The polymers with pendant phosphonic acid groups were soluble in polar solvents such as dimethyl sulfoxide and gave flexible and tough films via casting from solution. The polymers were hygroscopic and swelled in water. They did not decompose at temperatures of up to 260 °C under a nitrogen atmosphere.

Original languageEnglish
Pages (from-to)3770-3779
Number of pages10
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Issue number21
Publication statusPublished - 2001 Nov 1
Externally publishedYes


  • Functionalization of polymers
  • Ionomers
  • Membranes
  • Phosphonate ester
  • Phosphonic acid
  • Poly(arylene ether)
  • Polymer electrolytes

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry


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