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Pure Appl. Chem., 2013, Vol. 85, No. 3, pp. 511-520

Published online 2012-08-15

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

Pascal Dimitrov Raytchev, Céline Besset, Etienne Fleury, Jean-Pierre Pascault, Julien Bernard and Eric Drockenmuller*

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

Abstract: 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.