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

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72 Citations (Scopus)

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

ASJC Scopus subject areas

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

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    Nulwala, H., Takizawa, K., Odukale, A., Khan, A., Thibault, R. J., Taft, B. R., Lipshutz, B. H., & 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