Cellulose phenylcarbamate-derived hybrid bead-type chiral packing materials for efficient chiral recognition
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ORIGINAL RESEARCH
Cellulose phenylcarbamate-derived hybrid bead-type chiral packing materials for efficient chiral recognition Geng Li . Xiao Dai . Yixuan Min . Chang Yu . Tomoyuki Ikai . Lili Zhang . Jun Shen . Yoshio Okamoto
Received: 27 July 2020 / Accepted: 4 October 2020 Ó Springer Nature B.V. 2020
Abstract For efficient enantioseparation, eight organic–inorganic hybrid bead-type chiral packing materials (CPMs) with high organic contents have been developed using cellulose tris(3,5dimethylphenylcarbamates) bearing small amount of 3-(triethoxysilyl)propyl groups and tetraethyl orthosilicate by a modified Sto¨ber process in the basic condition. The hybrid beads could be formed more
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10570-020-03514-x) contains supplementary material, which is available to authorized users.
efficiently in the basic condition without using surfactant, compared to that in the acidic condition. The preparation conditions, including type and amount of catalyst, amount of water and temperature, significantly affected the organic contents and morphology of the hybrid CPMs. Their chiral recognition properties were then examined by high-performance liquid chromatography. The obtained hybrid CPMs with a higher organic content possessed better enantioseparation ability than the traditional CPMs and previous analogue derived from the acidic condition. For some racemates, the hybrid CPMs exhibited even higher enantioselectivity than the commercial Chiralpak IB N, which is one of the most powerful immobilized-type CPMs and prepared from cellulose tris(3,5-dimethylphenylcarbamate).
G. Li X. Dai Y. Min C. Yu L. Zhang (&) J. Shen (&) Y. Okamoto Key Laboratory of Superlight Materials and Surface Technology, Polymer Materials Research Center, College of Materials Science and Chemical Engineering, Harbin Engineering University, Ministry of Education, Harbin 150001, China e-mail: [email protected] J. Shen e-mail: [email protected] T. Ikai Y. Okamoto Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan
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Cellulose
Graphic abstract
Keywords Chiral recognition Enantioseparation Chiral packing materials Chiral separation HPLC Hybrid bead
Introduction As a type of renewable and abundant polymers from the nature, polysaccharides inherently possess regular helical structure and can be readily derivatized to afford various functional materials via polymer reactions using suitable reagents. One of their important applications is to prepare chiral packing materials (CPMs) for the enantioseparation of chiral compounds. Among many CPMs so far developed, cellulose phenylcarbamates bearing various substituents exhibited high enantioseparation ability to a variety of racemic compounds [Carreira and Yamamoto 2012; Okamoto 2009; Yashima et al. 2013]. A large series of CPMs derived from these derivatives have been developed, and owing to their excellent resolution powe
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