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

doi:10.1021/ma900892h

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 journal › Article › peer-review

76 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 language	English
Pages (from-to)	6068-6074
Number of pages	7
Journal	Macromolecules
Volume	42
Issue number	16
DOIs	https://doi.org/10.1021/ma900892h
Publication status	Published - 2009 Aug 25
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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10.1021/ma900892h

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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.",

author = "Hunaid Nulwala and Kenichi Takizawa and Anika Odukale and Anzar Khan and Thibault, {Raymond J.} and Taft, {Benjamin R.} and Lipshutz, {Bruce H.} and Hawker, {Craig J.}",

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T1 - Synthesis and characterization of isomeric vinyl-1,2,3-triazole materials by azide - Alkyne click chemistry

AU - Nulwala, Hunaid

AU - Takizawa, Kenichi

AU - Odukale, Anika

AU - Khan, Anzar

AU - Thibault, Raymond J.

AU - Taft, Benjamin R.

AU - Lipshutz, Bruce H.

AU - Hawker, Craig J.

PY - 2009/8/25

Y1 - 2009/8/25

N2 - 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.

AB - 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.

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ER -

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

Abstract

ASJC Scopus subject areas

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