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Solving the loss of orthogonality during the polyaddition of α-azide-ω-alkyne monomers catalyzed by Cu(PPh3)3Br: Application to the synthesis of high-molar mass polytriazoles

Authors

  • Sandra Binauld,

    1. Université Claude Bernard Lyon 1, INSA de Lyon, Ingénierie des Matériaux Polymères, (IMP, UMR CNRS 5223), 15 Boulevard Latarjet, 69622 Villeurbanne Cedex, France
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  • Etienne Fleury,

    1. Université Claude Bernard Lyon 1, INSA de Lyon, Ingénierie des Matériaux Polymères, (IMP, UMR CNRS 5223), 15 Boulevard Latarjet, 69622 Villeurbanne Cedex, France
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  • Eric Drockenmuller

    Corresponding author
    1. Université Claude Bernard Lyon 1, INSA de Lyon, Ingénierie des Matériaux Polymères, (IMP, UMR CNRS 5223), 15 Boulevard Latarjet, 69622 Villeurbanne Cedex, France
    • Université Claude Bernard Lyon 1, Ingénierie des Matériaux Polymères, (IMP, UMR CNRS 5223), 15 Boulevard Latarjet, 69622 Villeurbanne Cedex, France
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Abstract

Polyaddition of an α-azide-ω-alkyne monomer by Cu(PPh3)3Br catalyzed 1,3-dipolar cycloaddition was thoroughly studied as a model system to investigate the orthogonality of this click chemistry process. Indeed, loss of chain-end functionality and occurrence of side reactions have a tremendous impact on the molar mass of polymers obtained by step growth polymerization. Particularly, SEC, 1H, and 31P NMR experiments have highlighted the occurrence of a Staudinger side-reaction between azide chain-ends and PPh3 from the copper(I) catalyst that dramatically alters Mn of the resulting polytriazoles. A significant enhancement of Mn could be achieved by using an alternative catalyst and optimized experimental conditions, that is, dilution and reaction time. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 2470–2476, 2010

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