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

- 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.