Pure Appl. Chem., 2013, Vol. 85, No. 3, pp. 511-520
http://dx.doi.org/10.1351/PAC-CON-12-03-11
Published online 2012-08-15
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 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.