Synthesis and characterization of isomeric vinyl-1,2,3-triazole materials by azide - Alkyne click chemistry

Hunaid Nulwala, Kenichi Takizawa, Anika Odukale, Anzar Khan, Raymond J. Thibault, Benjamin R. Taft, Bruce H. Lipshutz, Craig J. Hawker

Research output: Contribution to journalArticle

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Abstract

The synthesis of isomeric, functionalized 4-vinyl-1,2,3-triazole and 5-vinyl-1,2,3-triazole monomers is demonstrated using heterogeneous copper (copper-in-charcoal)-catalyzed azide - alkyne cycloaddition (CuAAC) or homogeneous ruthenium (Ru)-catalyzed azide - alkyne cycloadditions (RuAAC) "click" protocols. These reactions are regiospecific, exclusively forming 1,4- and 1,5-disubstituted triazoles as determined by 1H NMR, 13C NMR, and X-ray crystallography analysis. Polymerizations were performed using living free radical procedures to yield materials with divergent properties. In the case of the 1,5-triazole materials, glass transition temperature were significantly higher that for the 1,4-derivatives while solubility was decreased.

Original languageEnglish
Pages (from-to)6068-6074
Number of pages7
JournalMacromolecules
Volume42
Issue number16
DOIs
Publication statusPublished - 2009 Aug 25
Externally publishedYes

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Triazoles
Alkynes
Azides
Cycloaddition
Nuclear magnetic resonance
Copper
Charcoal
X ray crystallography
Ruthenium
Free radicals
Solubility
Monomers
Polymerization
Derivatives
Free Radicals
Glass transition temperature

ASJC Scopus subject areas

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

Cite this

Nulwala, H., Takizawa, K., Odukale, A., Khan, A., Thibault, R. J., Taft, B. R., ... Hawker, C. J. (2009). Synthesis and characterization of isomeric vinyl-1,2,3-triazole materials by azide - Alkyne click chemistry. Macromolecules, 42(16), 6068-6074. https://doi.org/10.1021/ma900892h

Synthesis and characterization of isomeric vinyl-1,2,3-triazole materials by azide - Alkyne click chemistry. / Nulwala, Hunaid; Takizawa, Kenichi; Odukale, Anika; Khan, Anzar; Thibault, Raymond J.; Taft, Benjamin R.; Lipshutz, Bruce H.; Hawker, Craig J.

In: Macromolecules, Vol. 42, No. 16, 25.08.2009, p. 6068-6074.

Research output: Contribution to journalArticle

Nulwala, H, Takizawa, K, Odukale, A, Khan, A, Thibault, RJ, Taft, BR, Lipshutz, BH & Hawker, CJ 2009, 'Synthesis and characterization of isomeric vinyl-1,2,3-triazole materials by azide - Alkyne click chemistry', Macromolecules, vol. 42, no. 16, pp. 6068-6074. https://doi.org/10.1021/ma900892h
Nulwala, Hunaid ; Takizawa, Kenichi ; Odukale, Anika ; Khan, Anzar ; Thibault, Raymond J. ; Taft, Benjamin R. ; Lipshutz, Bruce H. ; Hawker, Craig J. / Synthesis and characterization of isomeric vinyl-1,2,3-triazole materials by azide - Alkyne click chemistry. In: Macromolecules. 2009 ; Vol. 42, No. 16. pp. 6068-6074.
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