Reference : New developments in the functionalization of aliphatic polyesters by "click" copper-c...
Scientific congresses and symposiums : Unpublished conference
Physical, chemical, mathematical & earth Sciences : Chemistry
Engineering, computing & technology : Materials science & engineering
http://hdl.handle.net/2268/21039
New developments in the functionalization of aliphatic polyesters by "click" copper-catalyzed azide-alkyne cycloaddition
English
Lecomte, Philippe mailto [Université de Liège - ULg > Département de chimie (sciences) > Centre d'études et de rech. sur les macromolécules (CERM) >]
Riva, Raphaël [Université de Liège - ULg > Département de chimie (sciences) > Centre d'études et de rech. sur les macromolécules (CERM) >]
Schmeits, Stephanie [Université de Liège - ULg > Département de chimie (sciences) > Centre d'études et de rech. sur les macromolécules (CERM) >]
Croisier, Florence [Université de Liège - ULg > Département de chimie (sciences) > Centre d'études et de rech. sur les macromolécules (CERM) >]
Grignard, Bruno [Université de Liège - ULg > Département de chimie (sciences) > Centre d'études et de rech. sur les macromolécules (CERM) >]
Jérôme, Robert mailto [Université de Liège - ULg > Département de chimie (sciences) > Département de chimie (sciences) >]
Jérôme, Christine mailto [Université de Liège - ULg > Département de chimie (sciences) > Centre d'études et de rech. sur les macromolécules (CERM) - Chimie des macromolécules et des matériaux organiques >]
3-Jun-2009
1
No
Yes
International
EUPOC2009, EPF Europolymer Conference, "Click" - Methods in Polymer and Materials Science
31/05/2009 - 4/06/2009
Wolfgang H. Binder, Søren Hvilsted
Gargnano
Italy
[en] click chemistry ; copper-mediated Huisgen's cycloaddition ; polymer functionalization
[en] Nowadays, biodegradable and biocompatible aliphatic polyesters are widely used as environmentally friendly thermoplastics and biomaterials. Nevertheless, the absence of any pendant functional group is a severe limitation for the development of novel applications. Our strategy aiming at functionalizing aliphatic polyesters relies on the “click” copper-catalyzed cycloaddition (CuAAC) of alkynes duly substituted by functional groups or even chains onto PCL bearing pendant azides. The aliphatic polyesters bearing pendant azides have been very efficiently synthesized by a straightforward approach, which relies on the ring-opening copolymerization of αClεCL (or γBrεCL) and εCL (or lactide) followed by reaction with sodium azide to convert pendant chlorides or bromides into azides. The alternative reported by Emrick et al. is based on the CuAAC reaction of azides substituted by any functional group onto copolyesters of poly(ε-caprolactone) bearing pendant alkynes. Interestingly enough, Emrick et al. carried out the CuAAc reaction in water at 80°C. Unfortunately, it turned out, at least in our hands, that these conditions can not be extended to the derivatization of more sensitive aliphatic polyesters because degradation was then unavoidable. Nevertheless, we found out that degradation can be minimized whenever the CuAAC reaction is carried out in an organic solvent at lower temperature. Typically, the CuAAC reaction was carried out in DMF or THF at 35°C. Recently, it was shown that supercritical carbon dioxide can be used as a more environmentally friendly solvent than DMF or THF.

The contamination by catalytic residues of aliphatic polyesters functionalized by the CuAAC reaction is a severe limitation in view of future applications, especially in the biomedical field. In the last part of this talk, a special attention will be paid on our current efforts to get rid of copper residues.
Center for Education and Research on Macromolecules (CERM)
Fonds de la Recherche Scientifique (Communauté française de Belgique) - F.R.S.-FNRS
Researchers
http://hdl.handle.net/2268/21039
This oral communication was presented by Philippe Lecomte

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