Synthesis and reactivity ratios of regioisomeric vinyl-1,2,3-triazoles with styrene

Michael Lartey, Martijn Gillissen, Brian J. Adzima, Kenichi Takizawa, David R. Luebke, Hunaid B. Nulwala

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

The free radical reactivity ratios between styrene and different vinyl-1,2,3-triazole regioisomeric monomers in 1,4-dioxane at 65 °C have been established using nonlinear least square method. The results obtained for the reactivity ratio between regioisomers show exceptionally different polymerization behavior, highlighting the effects of the electronic and steric factors of these regioisomeric monomers. The experimental results highlight the effects of the electronic and sterics on the copolymerization behavior. In case of 1,4-vinyl-triazoles, it was found that without the steric effects, the reactivity is very similar to that of styrene and forms random copolymers. However, it was found that 1,5-vinyl-triazoles are more reactive than 1,4-vinyl triazoles. In the case of styrene-co-1,4-vinyl-1,2,3-triazoles, the reactivity ratios were calculated to be rstyrene: r 1-octyl-4-vinyl-triazole = 1.97:0.54, rstyrene: r 1-benzyl-4-vinyl-triazole = 1.62:0.50, and rstyrene: r1-methyl-4-vinyl-triazole = 0.90:0.87. On the other hand, reactivity ratios for styrene-co-1,5-vinyl-1,2,3-triazoles were found to be r styrene: r1-octyl-5-vinyl-triazole = 0.13:0.66 and r styrene: r1-benzyl-5-vinyl-triazole = 0.34:0.49.

Original languageEnglish
Pages (from-to)3359-3364
Number of pages6
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume51
Issue number16
DOIs
Publication statusPublished - 15 Aug 2013
Externally publishedYes

Keywords

  • Mayo-Lewis equation
  • click chemistry
  • copolymerization
  • nonlinear least squares (NLLS)
  • radical polymerization
  • reactivity ratio
  • vinyl-1,2,3-triazole

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