Homochiral MOF–Polymer Mixed Matrix Membranes for Efficient Separation of Chiral Molecules

Yizhihao Lu; Huacheng Zhang; Jun Yong Chan; Ranwen Ou; Haijin Zhu; Maria Forsyth; Emilia M. Marijanovic; Cara M. Doherty; Philip J. Marriott; Mark M.Banaszak Holl; Huanting Wang

doi:10.1002/anie.201910408

Homochiral MOF–Polymer Mixed Matrix Membranes for Efficient Separation of Chiral Molecules

Yizhihao Lu, Huacheng Zhang^*, Jun Yong Chan, Ranwen Ou, Haijin Zhu, Maria Forsyth, Emilia M. Marijanovic, Cara M. Doherty, Philip J. Marriott, Mark M.Banaszak Holl, Huanting Wang

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

148 Scopus citations

Abstract

Homochiral metal–organic framework (MOF) membranes have been recently reported for chiral separations. However, only a few high-quality homochiral polycrystalline MOF membranes have been fabricated due to the difficulty in crystallization of a chiral MOF layer without defects on porous substrates. Alternatively, mixed matrix membranes (MMMs), which combine potential advantages of MOFs and polymers, have been widely demonstrated for gas separation and water purification. Here we report novel homochiral MOF–polymer MMMs for efficient chiral separation. Homochirality was successfully incorporated into achiral MIL-53-NH₂ nanocrystals by post-synthetic modification with amino acids, such as l-histidine (l-His) and l-glutamic acid (l-Glu). The MIL-53-NH-l-His and MIL-53-NH-l-Glu nanocrystals were then embedded into polyethersulfone (PES) matrix to form homochiral MMMs, which exhibited excellent enantioselectivity for racemic 1-phenylethanol with the highest enantiomeric excess value up to 100 %. This work, as an example, demonstrates the feasibility of fabricating diverse large-scale homochiral MOF-based MMMs for chiral separation.

Original language	English
Pages (from-to)	16928-16935
Number of pages	8
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	47
DOIs	https://doi.org/10.1002/anie.201910408
State	Published - 18 Nov 2019
Externally published	Yes

Keywords

chiral resolution
chirality
homochiral membrane separation
metal–organic frameworks
mixed-matrix membrane

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10.1002/anie.201910408

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title = "Homochiral MOF–Polymer Mixed Matrix Membranes for Efficient Separation of Chiral Molecules",

abstract = "Homochiral metal–organic framework (MOF) membranes have been recently reported for chiral separations. However, only a few high-quality homochiral polycrystalline MOF membranes have been fabricated due to the difficulty in crystallization of a chiral MOF layer without defects on porous substrates. Alternatively, mixed matrix membranes (MMMs), which combine potential advantages of MOFs and polymers, have been widely demonstrated for gas separation and water purification. Here we report novel homochiral MOF–polymer MMMs for efficient chiral separation. Homochirality was successfully incorporated into achiral MIL-53-NH2 nanocrystals by post-synthetic modification with amino acids, such as l-histidine (l-His) and l-glutamic acid (l-Glu). The MIL-53-NH-l-His and MIL-53-NH-l-Glu nanocrystals were then embedded into polyethersulfone (PES) matrix to form homochiral MMMs, which exhibited excellent enantioselectivity for racemic 1-phenylethanol with the highest enantiomeric excess value up to 100 %. This work, as an example, demonstrates the feasibility of fabricating diverse large-scale homochiral MOF-based MMMs for chiral separation.",

keywords = "chiral resolution, chirality, homochiral membrane separation, metal–organic frameworks, mixed-matrix membrane",

author = "Yizhihao Lu and Huacheng Zhang and Chan, {Jun Yong} and Ranwen Ou and Haijin Zhu and Maria Forsyth and Marijanovic, {Emilia M.} and Doherty, {Cara M.} and Marriott, {Philip J.} and Holl, {Mark M.Banaszak} and Huanting Wang",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

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doi = "10.1002/anie.201910408",

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T1 - Homochiral MOF–Polymer Mixed Matrix Membranes for Efficient Separation of Chiral Molecules

AU - Lu, Yizhihao

AU - Zhang, Huacheng

AU - Chan, Jun Yong

AU - Ou, Ranwen

AU - Zhu, Haijin

AU - Forsyth, Maria

AU - Marijanovic, Emilia M.

AU - Doherty, Cara M.

AU - Marriott, Philip J.

AU - Holl, Mark M.Banaszak

AU - Wang, Huanting

PY - 2019/11/18

Y1 - 2019/11/18

N2 - Homochiral metal–organic framework (MOF) membranes have been recently reported for chiral separations. However, only a few high-quality homochiral polycrystalline MOF membranes have been fabricated due to the difficulty in crystallization of a chiral MOF layer without defects on porous substrates. Alternatively, mixed matrix membranes (MMMs), which combine potential advantages of MOFs and polymers, have been widely demonstrated for gas separation and water purification. Here we report novel homochiral MOF–polymer MMMs for efficient chiral separation. Homochirality was successfully incorporated into achiral MIL-53-NH2 nanocrystals by post-synthetic modification with amino acids, such as l-histidine (l-His) and l-glutamic acid (l-Glu). The MIL-53-NH-l-His and MIL-53-NH-l-Glu nanocrystals were then embedded into polyethersulfone (PES) matrix to form homochiral MMMs, which exhibited excellent enantioselectivity for racemic 1-phenylethanol with the highest enantiomeric excess value up to 100 %. This work, as an example, demonstrates the feasibility of fabricating diverse large-scale homochiral MOF-based MMMs for chiral separation.

AB - Homochiral metal–organic framework (MOF) membranes have been recently reported for chiral separations. However, only a few high-quality homochiral polycrystalline MOF membranes have been fabricated due to the difficulty in crystallization of a chiral MOF layer without defects on porous substrates. Alternatively, mixed matrix membranes (MMMs), which combine potential advantages of MOFs and polymers, have been widely demonstrated for gas separation and water purification. Here we report novel homochiral MOF–polymer MMMs for efficient chiral separation. Homochirality was successfully incorporated into achiral MIL-53-NH2 nanocrystals by post-synthetic modification with amino acids, such as l-histidine (l-His) and l-glutamic acid (l-Glu). The MIL-53-NH-l-His and MIL-53-NH-l-Glu nanocrystals were then embedded into polyethersulfone (PES) matrix to form homochiral MMMs, which exhibited excellent enantioselectivity for racemic 1-phenylethanol with the highest enantiomeric excess value up to 100 %. This work, as an example, demonstrates the feasibility of fabricating diverse large-scale homochiral MOF-based MMMs for chiral separation.

KW - chiral resolution

KW - chirality

KW - homochiral membrane separation

KW - metal–organic frameworks

KW - mixed-matrix membrane

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U2 - 10.1002/anie.201910408

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ER -

Homochiral MOF–Polymer Mixed Matrix Membranes for Efficient Separation of Chiral Molecules

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