Synthesis and Characterization of Isomeric Vinyl-1,2,3-triazole Materials by Azide−Alkyne Click Chemistry

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” protoc...

Full description

Saved in:
Bibliographic Details
Published in:Macromolecules 2009-08, Vol.42 (16), p.6068-6074
Main Authors: Nulwala, Hunaid, Takizawa, Kenichi, Odukale, Anika, Khan, Anzar, Thibault, Raymond J, Taft, Benjamin R, Lipshutz, Bruce H, Hawker, Craig J
Format: Article
Language:English
Subjects:
Applied sciences
Exact sciences and technology
Model compounds
Organic polymers
Physicochemistry of polymers
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0024-9297
1520-5835
DOI:10.1021/ma900892h