Development And Application Of Novel Cyclodextrin Chiral Separation Materials In High Performance Liquid Chromatography

In order to improve the application of cyclodextrin chiral separation materials(CD-CSMs),a series of novel CD-CSMs were prepared and applied to enantioseparation based on the development of CSMs.The effects of CD functional groups,bonding arms and other factors on enantioseparation were investigated.In addition,the design of chiral stationary phase was innovated from the material type in view of the saturation of the original species of CSMs.(1)N₃-CD-CSM(CSM1)was modified with L-propargylglycine,propargylamine and 3-butynoic acid via“Click Chemistry”reaction,respectively.The prepared CD-CSMs were characterized by a series of techniques.After the characterization,the enantioseparation ability of these CD-CSMs have been evaluated in high performance liquid chromatography(HPLC)by nearly fifty enantiomers including dansyl amino acids,chiral lactides and diktones.Most of these enantiomers were separated on the prepared CD-CSMs with a good resolution and selectivity.Through the analyzation of experimental data,the chiral recognition and separation ability of CD-CSMs were strongly affected by CD functional groups.Apart from this,the inclusion interaction between cyclodextrin and guest molecules were further investigated by fluorescence inclusion technology.(2)New linkages with similar structure were prepared by the modification of amino silane coupling agent with propiolic acid,4-pentynoic acid and 6-heptynoic acid via amidation reaction respectively.The surface activated silica were modified with these alkynyl silane coupling agents.By“Azido-Alkyl”click chemistry reaction,the mono-(6^A-azido-6^A-deoxy)-?-CD were bonded onto the surface of alkyl silica and three native CD-CSMs including CSM5,CSM6 and CSM7,were synthesized.Enantioseparation efficiency of the prepared CD-CSMs were investigated by the separation of a series of racemates including isoxazolines,chiral lactides and chiral diktones in HPLC.It can be known from the experiment results that the length of linkage can affect the enantioseparation of CD-CSMs seriesly.And the suitable linkage length of CD-CSM for different samples is different.(3)In this article,we made an innovative attempt on the novel CSMs.By developing new synthetic routes of the COF-Si O₂composite,a new material COF_DB-rGO@Si O₂were prepared.And through kinds of characteristic technologies were applied to characterize its structure and morphology including Attenuated Total Reflectance-Fourier transform Infrared spectroscopy(ATR-FTIR),Nuclear Magnetic Resonance(NMR),X-ray Photoelectron Spectroscopy(XPS)and Scanning Electron Microscope(SEM).And through the experimental data,it demonstrated that the morphology of product COF_DB-rGO@Si O₂was layer-by-layer encapsulated spherical structure with Si O₂core.Though it didn't behave enough chemical stable.It still paves a new way to prepare the composite a COF and Si O₂and application of COFs in HPLC.