Clicking Pentafluorostyrene Copolymers: Synthesis, Nanoprecipitation, and Glycosylation

被引:186
作者
Becer, C. Remzi [1 ,2 ,3 ]
Babiuch, Krzysztof [1 ]
Pilz, David [1 ]
Hornig, Stephanie [4 ]
Heinze, Thomas [4 ]
Gottschaldt, Michael [1 ,3 ]
Schubert, Ulrich S. [1 ,2 ,3 ]
机构
[1] Univ Jena, Lab Organ & Macromol Chem, D-07743 Jena, Germany
[2] Eindhoven Univ Technol, Lab Macromol Chem & Nanosci, NL-5600 MB Eindhoven, Netherlands
[3] Dutch Polymer Inst, NL-5612 AB Eindhoven, Netherlands
[4] Univ Jena, Ctr Excellence Polysaccharide Res, D-07743 Jena, Germany
关键词
FREE-RADICAL POLYMERIZATION; FRAGMENTATION CHAIN TRANSFER; WELL-DEFINED GLYCOPOLYMER; DRUG-DELIVERY; NANOPARTICLES; NITROXIDE; CHEMISTRY; EFFICIENT; ACRYLATE; CYCLOADDITION;
D O I
10.1021/ma9000176
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Glycopolymers consisting of styrene (St) and pentafluorostyrene (PFS) were synthesized by a combination of nitroxide-mediated polymerization and "click" chemistry. A series of well-defined homopolymers as well as block and random copolymers of St and PFS were obtained with different ratios by using Bloc Builder as an alkoxyamine initiator. Some copolymers showed self-assembly behavior into regular nanospheres with diameters ranging from 70 to 720 nm by applying the nanoprecipitation technique. In addition, a thiol-glycoside (2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranose) was reacted under ambient conditions with PFS moieties on the polymeric backbone utilizing a thiol-para fluoro "click" reaction. This. nucleophilic substitution reaction was performed with high yields, and the reaction kinetic was monitored online with F-19 NMR spectroscopy. Finally, the deacetylation of the protected glucose moieties was carried out to yield well-defined glycopolymers. The polymers were characterized in detail by H-1, C-13, and F-19 NMR spectroscopy, size exclusion chromatography, and MALDI TOF-MS.
引用
收藏
页码:2387 / 2394
页数:8
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