Mechanism of polymerization reaction of 2, 5-bis(tetrahydrothiopheniomethyl)furan dichloride. Effect of aromatic resonance energy on the polymerization of bis(sulfonium) salts

Bong Rae Cho, Tae Hoon Kim, Kyung Hwa Son, Yong Kwan Kim, Yun Kyong Lee, Seung Joon Jeon

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

The mechanism of polymerization reaction of 2, 5-bis(tetrahydrothiopheniomethyl)furan dichloride was studied kinetically. The reaction proceeds by the (Elcb)jn- mechanism to afford a 2, 5dihydrofuran intermediate M, which undergoes a free radical polymerization reaction. Comparison of the kinetic results reveals that the rate of elimination reaction increases, whereas that for the subsequent polymerization reaction decreases as the aromatic moiety of the bis(sulfonium) salts is changed from phenyl to thiophene to furan. The results have been attributed to the decreased resonance energy of the aromatic rings.

Original languageEnglish
Pages (from-to)8167-8172
Number of pages6
JournalMacromolecules
Volume33
Issue number22
DOIs
Publication statusPublished - 2000

ASJC Scopus subject areas

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

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