Poly(norbornenyl azlactone) as a versatile platform for sequential double click postpolymerization modification
| Autor: | Gwénaël Forcher, Laurent Fontaine, Francesca François, Clémence Nicolas, Véronique Montembault |
|---|---|
| Přispěvatelé: | Institut des Molécules et Matériaux du Mans (IMMM), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Cyclopentadiene Polymers and Plastics [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry General Physics and Astronomy chemistry.chemical_element 02 engineering and technology Polymer ROMP 010402 general chemistry 021001 nanoscience & nanotechnology Metathesis 01 natural sciences 0104 chemical sciences Ruthenium Catalysis chemistry.chemical_compound [CHIM.POLY]Chemical Sciences/Polymers Monomer chemistry Polymerization Polymer chemistry Materials Chemistry 0210 nano-technology |
| Zdroj: | European Polymer Journal European Polymer Journal, Elsevier, 2020, 141, pp.110081. ⟨10.1016/j.eurpolymj.2020.110081⟩ |
| ISSN: | 0014-3057 1873-1945 |
| DOI: | 10.1016/j.eurpolymj.2020.110081 |
| Popis: | International audience; Ring-opening metathesis polymerization (ROMP) of a heterofunctional azlactone-based monomer, namely norbornenyl azlactone (NBAzl), is reported for the first time using third generation ruthenium-based catalyst (G3′). It is demonstrated that ROMP of the mixture of stereoisomers of NBAzl obtained by Diels-Alder reaction between 2-vinyl-4,4-dimethyl-5-oxazolone (vinyl azlactone, VDM) and cyclopentadiene leads to well-defined polymers (Mn , SEC up to 52 500 g mol −1 , Ð < 1.37). The resulting polymers easily undergo click post-polymerization modification by aminolysis of the azlactone groups using amine nucleophiles. By using azido oligoethylene glycol amine, ROMP polymers having azido side-chains capable of alkyne azide click modification are prepared, that are not attainable by direct ROMP of azido-functionalized monomers. The successful clicking to the so-obtained azido-functional ROMP polymer was demonstrated by copper-catalyzed alkyne − azide cy-cloaddition (CuAAC) with alkyne-functionalized fluorescein. The reported versatile methodology produces with complete atom economy a platform for new functional polymer libraries, including polymer materials with potential medical and biological applications. |
| Databáze: | OpenAIRE |
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