title: N-Acylated chitosan bis(arylcarbamate)s: A class of promising chiral separation materials with powerful enantioseparation capability and high eluents tolerability.
abstract: In order to comprehensively understand the influence of coordination of the substituent at 2-position with those at 3- and 6-positions on the properties of chitosan derivatives, a series of chitosan 3,6-bis(arylcarbamate)-2-(amide)s (CACAs) and the related chiral stationary phases (CSPs) were prepared and reported in the present study. Specifically, chitosan was N-acylated with carboxylic acid anhydrides, and then further derivatized with various aryl isocyanates to afford CACAs, from which a class of coated-type CSPs were prepared. When the substituent introduced on the acyl group at 2-position and those on the phenyl group of the carbamates at 3- and 6-positions were fittingly combined, these prepared CACAs based CSPs would exhibit powerful chiral recognition ability, further resulting in a class of promising chiral separation materials with excellent enantioseparation performance. Meanwhile, these newly developed materials with suitable molecular weight also bear a high tolerability towards organic solvents, even including pure tetrahydrofuran, thus broadening their application in enantiomeric separation.
authors.affiliation: School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China.
authors.forename: Sheng
authors.initials: S
authors.lastname: Tang
authors.affiliation: School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China.
authors.forename: Jian-De
authors.initials: JD
authors.lastname: Liu
authors.affiliation: School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China.
authors.forename: Qin
authors.initials: Q
authors.lastname: Bin
authors.affiliation: School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China.
authors.forename: Ke-Qin
authors.initials: KQ
authors.lastname: Fu
authors.affiliation: School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China.
authors.forename: Xiao-Chen
authors.initials: XC
authors.lastname: Wang
authors.affiliation: School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China.
authors.forename: Ying-Bin
authors.initials: YB
authors.lastname: Luo
authors.affiliation: Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China.
authors.forename: Shao-Hua
authors.initials: SH
authors.lastname: Huang
authors.affiliation: School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China. Electronic address: zwbai@wit.edu.cn.
authors.forename: Zheng-Wu
authors.initials: ZW
authors.lastname: Bai
mesh_terms: D000215:Acylation; D048271:Chitosan / Q000031:analogs & derivatives* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D005663:Furans / Q000737:chemistry; D017953:Isocyanates / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism
chemical_list: D005663:Furans; D017953:Isocyanates; D012997:Solvents; C018674:tetrahydrofuran; D048271:Chitosan
keywords: Chiral separation materials; Chitosan; Enantioseparation capability; High-performance liquid chromatography; Solvent tolerability