Structure-Properties Relationship of Biosourced Stereocontrolled Polytriazoles from Click Chemistry Step Growth Polymerization of Diazide and Dialkyne Dianhydrohexitols

The design of dialkyne and diazide functionalized dianhydrohexitol stereoisomers (1-16) afforded a new family of starch-based polytriazoles (7-15) with defined stereochemistry through A(2) + B-2 CuAAC step. growth polymerization. The present strategy gave rise to polytriazoles having a high: biosourced weight fraction (superior to 60% wt) and exhibiting relatively high molar masses (M-n = 8-17 kg/mol) that could be easily dissolved in DMF or DMSO. The Obtained materials were amorphous and displayed high transition temperatures (T-g = 125-166 degrees C)as yell as good resistance to thermal degradation (T-d10 = 325-347 degrees C). Monomer stereochemistry proved to be a crucial parameter aiming at generating polymers with high T-g. Thus, optimal thermal properties were obtained With monomers having RR absolute configuration of the C-2 and C-5 carbon atoms (isomannide configuration).