Synthesis of perfluoroalkylene-vinylene-arylene copolymers via the Mizoroki-Heck co-polymerization of 1,4-divinylperfluorobutane and 1,6-divinylperfluorohexane with dihalogenated arylene monomers

Hiroto Tsukada, Tatsuro Hisa, Tomohiro Shirai, Toshiyuki Oshiki, Yoshiyuki Mizuhata, Norihiro Tokitoh, Hiroki Fukumoto, Tomohiro Agou

Research output: Contribution to journalArticlepeer-review

Abstract

Semi-fluorinated aromatic polymers containing perfluoroalkylene [-(CF2)n-, n = 4, 6], vinylene, and arylene units in their main chains were synthesized via the Mizoroki-Heck co-polymerization of 1,4-divinylperfluorobutane and 1,6-divinylperfluorohexane with arylene monomers. The co-polymerization of 1,4-divinylperfluorobutane and 1,4-diiodobenzene was catalyzed by a ligand-less Pd(OAc)2/Bu4NBr system (“Jeffrey conditions”), while a Herrmann-type palladacycle complex (“Herrmann's catalyst”) effectively catalyzed the co-polymerization of dibrominated arylene monomers (such as 1,4-dibromobenzene). The number-average molecular weights (Mn) and weight-average molecular weights (Mw) values of the synthesized semi-fluorinated aromatic polymers were in the ranges of 2.3 × 103 to 5.4 × 103 and 3.7 × 103 to 1.1 × 104, respectively. These polymers exhibited high thermal stability, as indicated by their 5% weight loss temperatures (Td5% up to 415 °C).

Original languageEnglish
Article number110033
JournalJournal of Fluorine Chemistry
Volume261-262
DOIs
Publication statusPublished - Sep 2022

Keywords

  • Mizorok-Heck co-polymerization
  • Perfluoroalkylene compounds
  • Semi-fluorinated aromatic polymers
  • Thermos-resistant polymers

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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