Engineering chiral porous metal-organic frameworks for enantioselective adsorption and separation

Yongwu Peng, Tengfei Gong, Kang Zhang, Xiaochao Lin, Yan Liu, Jianwen Jiang () and Yong Cui ()
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Yongwu Peng: School of Chemistry and Chemical Technology, Shanghai Jiao Tong University
Tengfei Gong: School of Chemistry and Chemical Technology, Shanghai Jiao Tong University
Kang Zhang: National University of Singapore
Xiaochao Lin: School of Chemistry and Chemical Technology, Shanghai Jiao Tong University
Yan Liu: School of Chemistry and Chemical Technology, Shanghai Jiao Tong University
Jianwen Jiang: National University of Singapore
Yong Cui: School of Chemistry and Chemical Technology, Shanghai Jiao Tong University

Nature Communications, 2014, vol. 5, issue 1, 1-9

Abstract: Abstract The separation of racemic molecules is of substantial significance not only for basic science but also for technical applications, such as fine chemicals and drug development. Here we report two isostructural chiral metal-organic frameworks decorated with chiral dihydroxy or -methoxy auxiliares from enantiopure tetracarboxylate-bridging ligands of 1,1′-biphenol and a manganese carboxylate chain. The framework bearing dihydroxy groups functions as a solid-state host capable of adsorbing and separating mixtures of a range of chiral aromatic and aliphatic amines, with high enantioselectivity. The host material can be readily recycled and reused without any apparent loss of performance. The utility of the present adsorption separation is demonstrated in the large-scale resolution of racemic 1-phenylethylamine. Control experiments and molecular simulations suggest that the chiral recognition and separation are attributed to the different orientations and specific binding energies of the enantiomers in the microenvironment of the framework.

Date: 2014
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DOI: 10.1038/ncomms5406

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