Reference : Contribution of "click chemistry" to the synthesis of antimicrobial aliphatic copolyester
Scientific journals : Article
Engineering, computing & technology : Materials science & engineering
Physical, chemical, mathematical & earth Sciences : Chemistry
http://hdl.handle.net/2268/3668
Contribution of "click chemistry" to the synthesis of antimicrobial aliphatic copolyester
English
Riva, Raphaël [University of Liège (ULg) > Department of Chemistry > Center for Education and Research on Macromolecules (CERM) > >]
Lussis, Perrine [University of Liège (ULg) > Department of Chemistry > Center for Education and Research on Macromolecules (CERM) > >]
Lenoir, Sandrine [University of Liège (ULg) > Department of Chemistry > Center for Education and Research on Macromolecules (CERM) > >]
Jérôme, Christine mailto [Université de Liège - ULg > Department of Chemistry > Center for Education and Research on Macromolecules (CERM) > >]
Jérôme, Robert mailto [University of Liège (ULg) > Department of Chemistry > Center for Education and Research on Macromolecules (CERM) > >]
Lecomte, Philippe mailto [University of Liège (ULg) > Department of Chemistry > Center for Education and Research on Macromolecules (CERM) > >]
15-Apr-2008
Polymer
Elsevier Science
49
8
2023-2028
Yes (verified by ORBi)
International
0032-3861
Oxford
United Kingdom
[en] ring-opening polymerization ; lactone ; click chemistry ; copper-mediated Huisgen's cycloaddition ; antimicrobial polymer ; polymer functionalization
[en] A straightforward strategy is proposed to impart antimicrobial properties to biodegradable poly(oxepan-2-one) (poly(epsilon-caprolactone) or PCL), which is based on the grafting of pendant ammonium salts by "click" chemistry. First, statistical copolymerization of 3-chlorooxepan-2-one (alpha-chloro-epsilon-caprolactone or alpha Cl epsilon CL) with oxepan-2-one (epsilon-caprolactone or epsilon CL) was initiated by 2,2-dibutyl-2-stanna-1,3-dioxepane (DSDOP). In a second step, pendant chlorides were converted into azides by reaction with sodium azide (NaN3). Finally, quaternary ammonium containing alkynes were quantitatively added to the pendant azide groups of PCL by the copper-catalyzed Huisgen's 1,3-dipolar cycloaddition, which is a typical "click" reaction. An alternative two-step strategy based on the cycloaddition of the amine containing alkyne onto the pendant azides, followed by quaternization turned out to be less efficient. The antimicrobial activity was analyzed by the "shaking flask method" in the presence of Escherichia coli
Center for Education and Research on Macromolecules (CERM)
Politique Scientifique Fédérale (Belgique) = Belgian Federal Science Policy ; Fonds de la Recherche Scientifique (Communauté française de Belgique) - F.R.S.-FNRS ; Fonds pour la formation à la Recherche dans l'Industrie et dans l'Agriculture (Communauté française de Belgique) - FRIA
Researchers
http://hdl.handle.net/2268/3668
10.1016/j.polymer.2008.03.008
http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6TXW-4S0PKF2-3-5&_cdi=5601&_user=532038&_orig=browse&_coverDate=04%2F15%2F2008&_sk=999509991&view=c&wchp=dGLbVlz-zSkWz&md5=be9ac4febaccbd96524bffd1781858a6&ie=/sdarticle.pdf
The authors acknowledge Polymer (Elsevier) for allowing them to archive this paper.

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