Structure−Properties Relationship of Biosourced Stereocontrolled Polytriazoles from Click Chemistry Step Growth Polymerization of Diazide and Dialkyne Dianhydrohexitols
| Autor: | Céline Besset, Etienne Fleury, Eric Drockenmuller, Julien Bernard, Jean-Pierre Pascault |
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| Rok vydání: | 2010 |
| Předmět: |
Azides
Chemical Phenomena Polymers and Plastics Polymers Bioengineering Catalysis Polymerization Dianhydrohexitol Biomaterials Structure-Activity Relationship chemistry.chemical_compound Sugar Alcohols Polymer chemistry Materials Chemistry Organic chemistry Thermal stability chemistry.chemical_classification Molar mass Molecular Structure Absolute configuration Stereoisomerism Polymer Triazoles Step-growth polymerization Monomer chemistry Cyclization Alkynes Click chemistry Click Chemistry Copper |
| Zdroj: | Biomacromolecules. 11:2797-2803 |
| ISSN: | 1526-4602 1525-7797 |
| DOI: | 10.1021/bm100872h |
| Popis: | The design of dialkyne and diazide functionalized dianhydrohexitol stereoisomers (1-6) 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 °C) as well as good resistance to thermal degradation (T(d10) = 325-347 °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). |
| Databáze: | OpenAIRE |
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