RAFT polymerization of bio-based 1-vinyl-4-dianhydrohexitol-1,2,3-triazole stereoisomers obtained via click chemistry

Article abstract of DOI:10.1021/bm301435e

Four 1-vinyl-4-dianhydrohexitol-1,2,3-triazole stereoisomers are prepared from isomannide, isoidide, and isosorbide using an alkylation/CuAAC-ligation/ elimination three-step strategy. After characterization of the monomers by NMR, differential scanning calorimetry (DSC), and high-resolution mass spectrometry (HRMS), the corresponding stereocontrolled poly(1-vinyl-4-dianhydrohexitol-1,2, 3-triazole)s are obtained by RAFT polymerization using a xanthate chain transfer agent. A systematic investigation of the structure-properties relationship of both the monomers and polymers highlights the significant impact of the dianhydrohexitols stereochemistry on their physical properties (¹H and ¹³C NMR chemical shifts, physical state, T_g, thermal stability and solubility). A particularly original and unexpected behavior is highlighted since the two different isosorbide-based poly(1-vinyl-4- dianhydrohexitol-1,2,3-triazole) stereoisomers exhibit contrasting solubility in water.