N-Acylated chitosan bis(arylcarbamate)s: A class of promising chiral separation materials with powerful enantioseparation capability and high eluents tolerability

• Published in: Journal of Chromatography A 2016-12, Vol.1476, p.53-62
• Main Authors: Tang, Sheng, Liu, Jian-De, Bin, Qin, Fu, Ke-Qin, Wang, Xiao-Chen, Luo, Ying-Bin, Huang, Shao-Hua, Bai, Zheng-Wu
• Format: Article
• Language: English
• Subjects: Chiral separation materials; Chitosan; Enantioseparation capability; High-performance liquid chromatography; Solvent tolerability
• ISSN: 0021-9673
• DOI: 10.1016/j.chroma.2016.11.016

•Chitosan 3,6-bis(arylcarbamate)-2-(amide)s (CACAs) were prepared and reported.•Appropriate substituents combination results in high enantioseparation capability.•The CACAs with suitable molecular weight (Mw) can bear a high eluents tolerability.•Substituents combination and Mw are key factors for the performances of the CACAs.•Structure-optimized CACAs are powerful for enantioseparation and eluents tolerance. 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.