Cyclodextrin metal-organic framework-polymer composite membranes towards ultimate and stable enantioselectivity

Lu, Yizhihao; Chan, Jun Yong; Zhang, Huacheng; Li, Xingya; Nolvachai, Yada; Marriott, Philip J.; Zhang, Xiwang; Simon, George P.; Holl, Mark M. Banaszak; Wang, Huanting

doi:10.1016/j.memsci.2020.118956

Cited by 49 publications

(41 citation statements)

References 41 publications

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“…Instead of a column, Lu and co-workers recently designed a composite membrane with CD-MOF-1 as the chiral selector and polyethersulfone (PES) as the matrix. 219 The synthesized MMM (CD-MOF/ PES) exhibited high enantioselectivity for the flavouring agent R-1phenylethanol, as is shown in Fig. 10j.…”

Section: Storage Separation and Removal Of Chemicalsmentioning

confidence: 82%

Cyclodextrin metal–organic frameworks and derivatives: recent developments and applications

et al. 2022

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Section: Storage Separation and Removal Of Chemicalsmentioning

confidence: 82%

Cyclodextrin metal–organic frameworks and derivatives: recent developments and applications

et al. 2022

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“…The same group recently reported a CD-MOF/PES MMM for chiral separation, which also exhibited excellent enantioselectivity toward 1-phenylethanol with the ee value up to 100%, and demonstrated a retarded transport mechanism. [118] It was found that when and c) Flux of two enantiomers of 1-phenylethanol through an L-His-ZIF-8 membrane versus time. Reproduced with permission.…”

Section: Hybrid Chiral Separation Membranesmentioning

confidence: 99%

Emerging Homochiral Porous Materials for Enantiomer Separation

Zhang

Zhu

et al. 2021

Adv Funct Materials

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Efficient resolution of racemates of chiral molecules is of great significance in the pharmaceutical, agrochemical, fragrances, and food additives industries. Emerging homochiral porous materials such as metal-organic frameworks, covalent-organic frameworks, porous-organic cages, and metal-organic cages with ultrahigh surface area, controllable pore chemistry and ample chiral recognition sites are promising for efficient chiral resolution, which display excellent properties for chiral separation applications. This review summarizes the design and synthesis strategies for the construction of homochiral porous materials, including direct synthesis, post-synthesis, and chiral induction synthesis. Following this, applications of emerging homochiral porous materials, including enantioselective adsorption, chiral chromatography, and membrane-based chiral separation are highlighted. Finally, the challenges in this area are discussed, with future perspectives provided.

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“…There are two suggested mechanisms for chiral resolution via membrane-based process: facilitated transport and retarded transport. Generally, enantioselective membranes can be divided into two classes: 'diffusion-selective' membranes and 'sorptionselective' membranes, which employ facilitated and retarded transport mechanisms, respectively [16,[40][41][42] (Figure 1). In a diffusion-selective membrane, one type of enantiomer with a higher binding affinity can dominantly interact with the chiral active sites in the membrane.…”

Section: Transport Mechanisms In Enantioselective Membranesmentioning

confidence: 99%

“…This ability is attributed to the 40 stereogenic centers present in each γ-CD torus [65]. The γ-CD-MOF based MMM (Figure 3) was prepared by adopting a procedure similar to preparing MIL-53-NH-L-His/PES: the mixture of γ-CD-MOF and PES solution was cast into a self-standing membrane [42]. The ee value of 100% for R-(+)-1-phenylethanol over S-(-)-1-phenylethanol was obtained with a non-polar solvent of n-hexane.…”

Section: Dispersed Chiral Mof Fillers In An Achiral Polymeric Matrixmentioning

confidence: 99%

“…As mentioned in Section 3, a cyclodextrin (CD)-MOF-based MMM and COF-based MMM were recently developed, and they achieved approximately 100% of ee value over 24 and 36 h, respectively. Such diffusion-selective MMMs could be one of the plausible options for continuous enantiomeric separation [42,74]. Various CD-based MOFs or COFs can be synthesized via reticular chemistry; thus, a new class of MOFs or COFs can be prepared for use as chiral fillers to develop versatile enantioselective MMMs.…”

Section: Prospects For Designing Enantioselective Mmmsmentioning

confidence: 99%

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Enantioselective Mixed Matrix Membranes for Chiral Resolution

2021

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Most pharmaceuticals are stereoisomers that each enantiomer shows dramatically different biological activity. Therefore, the production of optically pure chemicals through sustainable and energy-efficient technology is one of the main objectives in the pharmaceutical industry. Membrane-based separation is a continuous process performed on a large scale that uses far less energy than the conventional thermal separation process. Enantioselective polymer membranes have been developed for chiral resolution of pharmaceuticals; however, it is difficult to generate sufficient enantiomeric excess (ee) with conventional polymers. This article describes a chiral resolution strategy using a composite structure of mixed matrix membrane that employs chiral fillers. We discuss several enantioselective fillers, including metal-organic frameworks (MOFs), covalent organic frameworks (COFs), zeolites, porous organic cages (POCs), and their potential use as chiral fillers in mixed matrix membranes. State-of-the-art enantioselective mixed matrix membranes (MMMs) and the future design consideration for highly efficient enantioselective MMMs are discussed.

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Cyclodextrin metal-organic framework-polymer composite membranes towards ultimate and stable enantioselectivity

Cited by 49 publications

References 41 publications

Cyclodextrin metal–organic frameworks and derivatives: recent developments and applications

Cyclodextrin metal–organic frameworks and derivatives: recent developments and applications

Emerging Homochiral Porous Materials for Enantiomer Separation

Enantioselective Mixed Matrix Membranes for Chiral Resolution

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