1,4:3,6-Dianhydrohexitols: Original Platform for the Design of Biobased Polymers Using Robust, Efficient, and Orthogonal Chemistry

Pascal Dimitrov Raytchev (1) , Céline Besset (1) , Etienne Fleury (1) , Jean-Pierre Pascault (1) , Julien Bernard (1) , Eric Drockenmuller (1)

1 IMP - Ingénierie des Matériaux Polymères

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 stereo chemistry and cycloaddition regioselectivity on materials properties.

Mots clés: GLYCOLS; POLYMERS; POLYCONDENSATION; REACTIVITY (Chemistry); RING formation (Chemistry); REGIOSELECTIVITY (Chemistry)

Domaines: Polymères; Matériaux

Pascal Dimitrov Raytchev, Céline Besset, Etienne Fleury, Jean-Pierre Pascault, Julien Bernard, et al.. 1,4:3,6-Dianhydrohexitols: Original Platform for the Design of Biobased Polymers Using Robust, Efficient, and Orthogonal Chemistry. Pure and Applied Chemistry, 2013, 85, pp.511. ⟨10.1351/PAC-CON-12-03-11⟩. ⟨hal-00862369⟩