title: Cyclodextrin clicked chiral stationary phases with functionalities-tuned enantioseparations in high performance liquid chromatography.
abstract: In this work, two cyclodextrin (CD) chiral stationary phases (CSPs) have been developed by clicking per-4-chloro-3-methylphenylcarbamoylated mono-6(A)-azido-β-CD (CSP1) and per-5-chloro-2-methylphenylcarbamoylated mono-6(A)-azido-β-CD (CSP2) onto alkynylated silica support. The enantioslectivies of the as-obtained new CSPs have been evaluated using 29 model racemates including aromatic alcohols, flavonoids, β-blocker and FMOC-amino acids in both reversed-phase (RP) and normal-phase (NP) high performance liquid chromatography (HPLC). The CD functionalities tuned enantioselectivities were elucidated in different HPLC elution modes. Higher chiral resolutions were achieved in RP-elution mode with the aid of the inclusion complexation in comparison to NP-elution mode. The π-π stacking interaction and dipole-dipole interaction provided by phenylcarbamate moieties can also contribute to the enantioseparation.
authors.affiliation: College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China.
authors.forename: Yuzhou
authors.initials: Y
authors.lastname: Lin
authors.affiliation: College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China.
authors.forename: Jie
authors.initials: J
authors.lastname: Zhou
authors.affiliation: College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China.
authors.forename: Jian
authors.initials: J
authors.lastname: Tang
authors.affiliation: College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China. Electronic address: whtang@mail.njust.edu.cn.
authors.forename: Weihua
authors.initials: W
authors.lastname: Tang
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D057930:Click Chemistry; D003505:Cyclodextrins / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry; D012822:Silicon Dioxide / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000596:Amino Acids; D003505:Cyclodextrins; D005419:Flavonoids; D012822:Silicon Dioxide
keywords: Chiral stationary phase; Click chemistry; Cyclodextrin; Enantioselectivity