Mechanism of polymerization reaction of 2,5-bis(tetrahydrothiopheniomethyl)thiophene dichloride

Bong-Rae Cho, Tae Hoon Kim, Yong Kwan Kim, Nam Soo Kim

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The polymerization kinetics of 2,5-bis(tetrahydrothiopheniomethyl)thiophene dichloride were studied. The reaction proceeds via a 2,5-dihydrothiophene intermediate M. Results of kinetic and product studies revealed that the 1,6-elimination proceeded by an (E1cb)irr mechanism. The rate of the disappearance of M was not influenced by the addition of OH-, carbanions, and tetrahydrothiophene but was accelerated by S2O8 2- and inhibited by TEMPO. In addition, the reaction mixture exhibited an electron spin resonance signal with a g value of 2.003 G and induced the polymerization of acrylamide. These results indicated a free radical polymerization mechanism.

Original languageEnglish
Pages (from-to)3583-3589
Number of pages7
JournalMacromolecules
Volume32
Issue number11
DOIs
Publication statusPublished - 1999 Jun 1

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Thiophenes
Thiophene
Polymerization
Kinetics
Acrylamide
Free radical polymerization
Paramagnetic resonance
TEMPO
hydroxide ion
tetrahydrothiophene

ASJC Scopus subject areas

  • Materials Chemistry

Cite this

Mechanism of polymerization reaction of 2,5-bis(tetrahydrothiopheniomethyl)thiophene dichloride. / Cho, Bong-Rae; Kim, Tae Hoon; Kim, Yong Kwan; Kim, Nam Soo.

In: Macromolecules, Vol. 32, No. 11, 01.06.1999, p. 3583-3589.

Research output: Contribution to journalArticle

Cho, Bong-Rae ; Kim, Tae Hoon ; Kim, Yong Kwan ; Kim, Nam Soo. / Mechanism of polymerization reaction of 2,5-bis(tetrahydrothiopheniomethyl)thiophene dichloride. In: Macromolecules. 1999 ; Vol. 32, No. 11. pp. 3583-3589.
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