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Surface Click Reactions on Polymeric Nanocapsules for Versatile Functionalization

  作者 Baier, G; Siebert, JM; Landfester, K; Musyanovych, A  
  选自 期刊  Macromolecules;  卷期  2012年45-8;  页码  3419-3427  
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[摘要]One-step synthesis of poly(butyl cyanoacrylate-co-propargyl cyanoacrylate) (P(BCA/PCA)) and polyurethane (PUR) azide nanocapsules for direct covalent and variable functionalization is reported. The capsules in the size range between 230 and 350 nm were synthesized in an inverse (water-in-oil) miniemulsion system through either interfacial anionic polymerization (in the case of P(BCA/PCA)) or interfacial polyaddition reaction with 2,4-toluene diisocyanate (PUR azide). Surface functionalization of nanocapsules was achieved by different copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, which were carried out under mild and ambient conditions. Click reactions of rhodamine azide and anthracene azide to P(BCA-co-PCA) nanocapsules were performed for quantitative determination of the surface alkyne bonds. PUR-azide nanocapsules were functionalized with propiolic acid and fluorescent alkyne dye. The reaction kinetics between propiolic acid and the azide monomer was studied by H-1 NMR spectroscopy. Furthermore, the ftinctionalization of nanocapsules with propiolic acid was extended to copper-free azide-alkyne cycloaddition, thus making the system materials.

 
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