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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Weir, Ron / Stohner, Jürgen

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ISSN
1365-3075
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Volume 85, Issue 3 (Aug 2012)

Issues

1,4:3,6-Dianhydrohexitols: Original platform for the design of biobased polymers using robust, efficient, and orthogonal chemistry

Pascal Dimitrov Raytchev
  • Corresponding author
  • Université Claude Bernard Lyon 1, INSA de Lyon, Ingénierie des Matériaux Polymères (UMR CNRS 5223), 15 Boulevard Latarjet, 69622 Villeurbanne Cedex, France
/ Céline Besset
  • Corresponding author
  • Université Claude Bernard Lyon 1, INSA de Lyon, Ingénierie des Matériaux Polymères (UMR CNRS 5223), 15 Boulevard Latarjet, 69622 Villeurbanne Cedex, France
/ Etienne Fleury
  • Corresponding author
  • Université Claude Bernard Lyon 1, INSA de Lyon, Ingénierie des Matériaux Polymères (UMR CNRS 5223), 15 Boulevard Latarjet, 69622 Villeurbanne Cedex, France
/ Jean-Pierre Pascault
  • Corresponding author
  • Université Claude Bernard Lyon 1, INSA de Lyon, Ingénierie des Matériaux Polymères (UMR CNRS 5223), 15 Boulevard Latarjet, 69622 Villeurbanne Cedex, France
/ Julien Bernard
  • Corresponding author
  • Université Claude Bernard Lyon 1, INSA de Lyon, Ingénierie des Matériaux Polymères (UMR CNRS 5223), 15 Boulevard Latarjet, 69622 Villeurbanne Cedex, France
/ Eric Drockenmuller
  • Corresponding author
  • Université Claude Bernard Lyon 1, INSA de Lyon, Ingénierie des Matériaux Polymères (UMR CNRS 5223), 15 Boulevard Latarjet, 69622 Villeurbanne Cedex, France
Published Online: 2012-08-15 | DOI: https://doi.org/10.1351/PAC-CON-12-03-11

1,4:3,6-Dianhydrohexitols (DAHs) are nontoxic and sustainable diols that have been extensively applied as monomers for the preparation of polymer materials by step-growth polymerization processes. The presence of two reactive alcohol groups was exploited to design a library of symmetric and asymmetric stereocontrolled alkyne- and/or azide-functionalized AA/BB and AB monomers suitable for thermal or copper(I)-catalyzed azide-alkyne cycloaddition (TAAC and CuAAC). Step-growth polymerization of these monomers yielded a series of linear polytriazoles as well as partially biosourced networks using a combination of AB + A2B2 derivatives. Characterization of the resulting materials allowed for the establishment of a thorough structure–property relationship emphasizing the impact of monomer stereochemistry and cycloaddition regioselectivity on materials properties.

Keywords: 1,4:3,6-dianhydrohexitols; alkynes; atom economy; azides; biomaterials; biosources; click chemistry; cycloadditions; isoidide; isomannide; isosorbide; materials chemistry; monomers; polyadditions; polymer chemistry; renewability; step growth polymerization; stereochemistry; structure–property relationships

Conference

International Conference on Polymers and Organic Chemistry (POC 2012), 14th, Doha, Qatar, 2012-01-06–2012-01-09

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About the article

Published Online: 2012-08-15

Published in Print: 2012-08-15


Citation Information: Pure and Applied Chemistry, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-12-03-11. Export Citation

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