title: RAFT polymerization of bio-based 1-vinyl-4-dianhydrohexitol-1,2,3-triazole stereoisomers obtained via click chemistry.
abstract: 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, Tg, 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.
authors.affiliation: Université Claude Bernard Lyon 1, INSA de Lyon, Ingénierie des Matériaux Polymères (IMP-UMR CNRS 5223), 15 Boulevard Latarjet, 69622 Villeurbanne Cedex, France.
authors.forename: Samir
authors.initials: S
authors.lastname: Beghdadi
authors.forename: Imen
authors.initials: I
authors.lastname: Abdelhedi Miladi
authors.forename: Hatem
authors.initials: H
authors.lastname: Ben Romdhane
authors.forename: Julien
authors.initials: J
authors.lastname: Bernard
authors.forename: Eric
authors.initials: E
authors.lastname: Drockenmuller
mesh_terms: D000478:Alkylation; D001672:Biocompatible Materials / Q000138:chemical synthesis*; D002152:Calorimetry, Differential Scanning; D002384:Catalysis; D057930:Click Chemistry / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D058105:Polymerization; D011108:Polymers / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001672:Biocompatible Materials; D011108:Polymers; D014230:Triazoles