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

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 stepgrowth 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 azidealkyne 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. © 2012, IUPAC.