title: Functionalization of macroporous organic polymer monolith based on succinimide ester reactivity for chiral capillary chromatography: a cyclodextrin click approach.
abstract: 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.
authors.affiliation: Institut Chimie et Matériaux Paris Est - Equipe Systèmes Polymères Complexes, UMR 7182 CNRS - Université Paris Est, 2-8 rue Henri Dunant, 94320 Thiais, France.
authors.forename: Mohamed
authors.initials: M
authors.lastname: Guerrouache
authors.forename: Marie-Claude
authors.initials: MC
authors.lastname: Millot
authors.forename: Benjamin
authors.initials: B
authors.lastname: Carbonnier