Dicationic AC regioisomer cyclodextrins: mono-6A-ammonium-6C-alkylimidazolium-β-cyclodextrin chlorides as chiral selectors for enantioseparation

Yun Dai; Shuye Wang; Jianhua Wu; Jian Tang; Weihua Tang

doi:10.1039/C2RA21940A

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Dicationic AC regioisomer cyclodextrins: mono-6^A-ammonium-6^C-alkylimidazolium-β-cyclodextrin chlorides as chiral selectors for enantioseparation†

Yun Dai,^a Shuye Wang,^a Jianhua Wu,^a Jian Tang*^a and Weihua Tang*^a

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* Corresponding authors

^a Key Laboratory of Soft Chemistry and Functional Materials, Ministry of Education, Nanjing University of Science and Technology, Nanjing, P. R. China
E-mail: tangj2005@hotmail.com, whtang@mail.njust.edu.cn
Fax: (86) 25 8431 7311
Tel: (86) 25 8431 7311

Abstract

Dicationic cyclodextrins with AC regioisomer structure were prepared by monosubstitution of 6^A-azido-β-cyclodextrin with 2-mesitylenesulfonyl chloride and the Staudinger reaction. One family of the desired cyclodextrins, the 6^A-ammonium-6^C-butylimidazolium-β-cyclodextrin chlorides, demonstrated a good chiral recognition ability towards both acidic and even neutral racemates even at concentrations as low as 0.5 mM.

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Article information

DOI: https://doi.org/10.1039/C2RA21940A
Article type: Communication
Submitted: 29 Jun 2012
Accepted: 15 Oct 2012
First published: 16 Oct 2012

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RSC Adv., 2012,2, 12652-12656

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Dicationic AC regioisomer cyclodextrins: mono-6^A-ammonium-6^C-alkylimidazolium-β-cyclodextrin chlorides as chiral selectors for enantioseparation

Y. Dai, S. Wang, J. Wu, J. Tang and W. Tang, RSC Adv., 2012, 2, 12652 DOI: 10.1039/C2RA21940A

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