Enantioselective sorption of alcohols in a homochiral metal–organic framework

Suh, Kyungwon; Yutkin, Maxim; Dybtsev, Danil N.; Fedin, Vladimir P.; Kim, Kimoon

doi:10.1039/c1cc16209h

Cited by 102 publications

(71 citation statements)

References 39 publications

(29 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Chiral MOF catalysts with uniform active sites for enantioselective reactions have been developed based on functionalized chiral molecular (pre)catalysts [21][22][23][24][25][26][27][28][29][30] . In a handful of latest studies, the resolution of enantiomers (racemic alcohols and sulphoxides) with chiral MOFs via chromatography [31][32][33][34] , crystallization [35][36][37][38][39][40] and membrane 41,42 has been reported, but only few exhibit good chiral separation performance.…”

mentioning

confidence: 99%

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

et al. 2014

View full text Add to dashboard Cite

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 0 -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.

show abstract

mentioning

confidence: 99%

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

et al. 2014

View full text Add to dashboard Cite

show abstract

“…Chiral PCPs have attracted considerable attention because of their potential applications in chiral recognition [9,10,24]. It was demonstrated that chiral recognition of PCPs was attributed to the difference of accessibility of a chiral molecule to the interaction sites between D-and L-isomer by single crystal X-ray diffraction measurement [24].…”

Section: Chiral Recognitionmentioning

confidence: 99%

Synthesis of chiral porous coordination polymer that shows structural transformation induced by guest molecules

Kitao

Tokunaga

Umeyama

et al. 2015

Inorganica Chimica Acta

View full text Add to dashboard Cite

a b s t r a c tWe report the synthesis of a new chiral porous coordination polymer [Zn 2 {(R)-5,5 0 -BDA} 2 (dabco)] n ÁDMF (5,5 0 -BDA = 2,2 0 -dihydroxy-1,1 0 -binaphthalene-5,5 0 -dicarboxylic acid, dabco = 1,4-diazabicyclo[2.2.2] octane). This compound had one-dimensional (1D) channels which were occupied by DMF molecules. The hydroxyl groups on the surface of the channels acted as DMF interactive sites. Removal of DMF from the pores resulted in an amorphous solid. However, the apohost underwent a structural (amorphous-tocrystalline) transformation in response to the addition of guest molecules with amide groups. Interestingly, the observed degree of crystallinity was different for chiral amides, depending on the stereoisomer used.

show abstract

“…For example, an experimental single-crystal X-ray diffraction study also points to the host-guest interactions between a homochiral MOF and two enantiomers of a chiral alcohol as the key driving force for the enantioselective sorption of alcohols in the chiral framework. [111] Structure -property relations are important for generic insight and design guides for MOF synthesis. Molecular simulations are particularly suitable to 'screen' many materials in a very efficient manner.…”

Section: Molecular Simulation 593mentioning

confidence: 99%

Exploring new methods and materials for enantioselective separations and catalysis

Dubbeldam

Calero

Vlugt

2014

Molecular Simulation

View full text Add to dashboard Cite

In this article, we will review and highlight some recent computational work on enantioselective adsorption and catalysis in zeolites and metal-organic frameworks. The design, development and understanding of chiral structures will help expand the utility of nanoporous materials into chiral technology. The highlighted works are examples of how molecular simulations can provide a fundamental understanding of chirality in nanoporous materials. This understanding is essential to help in the design and development of next-generation enantioselective separation devices and catalysts.

show abstract

Enantioselective sorption of alcohols in a homochiral metal–organic framework

Abstract: Single-crystal X-ray diffraction study reveals the host-guest interactions between a homochiral metal-organic framework and two enantiomers of a chiral alcohol providing the key driving force for the enantioselective sorption of alcohols in the framework.

Cited by 102 publications

References 39 publications

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

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

Synthesis of chiral porous coordination polymer that shows structural transformation induced by guest molecules

Exploring new methods and materials for enantioselective separations and catalysis

Contact Info

Product

Resources

About