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

Yizhihao Lu, Huacheng Zhang, Jeffrey Chan, Ranwen Ou, Haijin Zhu, Maria Forsyth, Emilia Marijanovic, Cara M Doherty, Philip J. Marriot, Mark Banaszak Holl, Huanting Wang

Research output: Contribution to journalArticleResearchpeer-review

1 Citation (Scopus)

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 languageEnglish
Pages (from-to)16928-16935
Number of pages8
JournalAngewandte Chemie - International Edition
Volume58
Issue number47
DOIs
Publication statusPublished - 18 Nov 2019

Keywords

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

Cite this

@article{6fc3ed07d4964773ade33702609f311e,
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 Jeffrey Chan and Ranwen Ou and Haijin Zhu and Maria Forsyth and Emilia Marijanovic and Doherty, {Cara M} and Marriot, {Philip J.} and {Banaszak Holl}, Mark and Huanting Wang",
year = "2019",
month = "11",
day = "18",
doi = "10.1002/anie.201910408",
language = "English",
volume = "58",
pages = "16928--16935",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "Wiley-Blackwell",
number = "47",

}

Homochiral MOF–Polymer Mixed Matrix Membranes for Efficient Separation of Chiral Molecules. / Lu, Yizhihao; Zhang, Huacheng; Chan, Jeffrey; Ou, Ranwen; Zhu, Haijin; Forsyth, Maria; Marijanovic, Emilia; Doherty, Cara M; Marriot, Philip J.; Banaszak Holl, Mark; Wang, Huanting.

In: Angewandte Chemie - International Edition, Vol. 58, No. 47, 18.11.2019, p. 16928-16935.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

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

AU - Lu, Yizhihao

AU - Zhang, Huacheng

AU - Chan, Jeffrey

AU - Ou, Ranwen

AU - Zhu, Haijin

AU - Forsyth, Maria

AU - Marijanovic, Emilia

AU - Doherty, Cara M

AU - Marriot, Philip J.

AU - Banaszak Holl, Mark

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

UR - http://www.scopus.com/inward/record.url?scp=85074404134&partnerID=8YFLogxK

U2 - 10.1002/anie.201910408

DO - 10.1002/anie.201910408

M3 - Article

AN - SCOPUS:85074404134

VL - 58

SP - 16928

EP - 16935

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 47

ER -