Guerrouache Mohamed, Millot Marie-Claude, Carbonnier Benjamin
Institut Chimie et Matériaux Paris Est - Equipe Systèmes Polymères Complexes, UMR 7182 CNRS - Université Paris Est, 2-8 rue Henri Dunant, 94320 Thiais, France.
Macromol Rapid Commun. 2009 Jan 16;30(2):109-13. doi: 10.1002/marc.200800584. Epub 2008 Dec 16.
Macroporous cross-linked organic polymer based on N-acryloxysuccinimide (NAS) and ethylene dimethacrylate (EDMA) was prepared inside 75 µm id fused silica capillary as a functionalizable monolithic stationary phase for chromatographic applications. Succinimide groups on the monolith surface provide reactive sites able to react readily through standard electrophile-nucleophile chemistry. Propargylamine was used to prepare alkyne functionalized poly(NAS-co-EDMA). Onto this azido-reactive polymer surface was grafted β-cyclodextrin (CD) via a triazole ring utilizing the copper(I)-catalyzed 1,3-dipolar cyclo-addition reaction. Chemical characterization was performed in situ after each synthetic step by means of Raman spectroscopy. Good enantioseparations of flavanone enantiomers, chosen as test chiral compound, were achieved under reversed phase conditions by both capillary electrochromatography and nano-liquid chromatography (nano-LC) techniques. These results demonstrate the potentiality and usefulness of click chemistry in the preparation of β-CD containing chiral organic polymer monolith.
基于N-丙烯酰氧基琥珀酰亚胺（NAS）和二甲基丙烯酸乙烯酯（EDMA）的大孔交联有机聚合物在75 µm内径的熔融石英毛细管内制备，作为用于色谱应用的可功能化整体固定相。整体表面的琥珀酰亚胺基团提供了能够通过标准亲电体-亲核体化学容易反应的反应位点。炔丙胺用于制备炔基官能化的聚（NAS-co-EDMA）。利用铜（I）催化的1,3-偶极环加成反应，通过三唑环将β-环糊精（CD）接枝到这种叠氮基反应性聚合物表面。在每个合成步骤之后，通过拉曼光谱原位进行化学表征。通过毛细管电色谱和纳米液相色谱（nano-LC）技术，在反相条件下，作为测试手性化合物的黄烷酮对映体实现了良好的对映体分离。这些结果证明了点击化学在制备含β-CD的手性有机聚合物整体中的潜力和实用性。
