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Progress in Chemistry 2022, Vol. 34 Issue (2): 328-341 DOI: 10.7536/PC201249 Previous Articles   Next Articles

• Review •

New Porous Materials Used as Chiral Stationary Phase for Chromatography

Bo Tang, Wei Wang, Aiqin Luo()   

  1. Key Laboratory of Molecular Medicine and Biotherapy, School of Life Science, Beijing Institute of Technology,Beijing 100081, China
  • Received: Revised: Online: Published:
  • Contact: Aiqin Luo
  • Supported by:
    National Key R&D Program of China(2019YFA0904104)
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It is well established that enantiomers often exhibit different biological and pharmacological responses. However, enantiomers remain a challenge to separate and analyze due to their identical physical and chemical properties in an achiral environment. Research on specialized separation techniques continues to be developed to obtain optically pure compounds. The separation of enantiomers by chromatographic methods, such as high-performance liquid chromatography (HPLC), gas chromatography (GC), and capillary electrochromatography (CEC), has become one of increasingly important research contents in chemistry over the past few decades due to the demand for pharmaceuticals, agrochemical, and food analysis. The chiral stationary phase (CSP) is key to separating and analyzing chiral compounds for these chromatographic resolution methods. With the rapid development of materials science, diverse types of porous materials as CSP have been studied in recent years. This review mainly focuses on investigating chiral porous materials as CSP for high-performance liquid chromatography (HPLC), gas chromatography (GC), and capillary electrochromatography (CEC) over the past five years. The chiral porous materials include chiral metal-organic frameworks (CMOFs), chiral covalent organic frameworks (CCOFs), chiral porous organic cages (CPOCs), chiral metal-organic cages (CMOCs), chiral microporous organic networks (MONs), and chiral mesoporous silicas (CMSs). Chiral recognition mechanisms of novel chiral porous materials are also discussed briefly. Finally, the related problems and prospects for CSP were briefly discussed.

Contents

1 Introduction

2 CSP of HPLC

2.1 CMOFs used as CSP

2.2 CCOFs used as CSP

2.3 Other materials used as CSP

3 CSP of GC

3.1 CMOFs used as CSP

3.2 CPOCs used as CSP

3.3 CMOCs used as CSP

3.4 Other materials used as CSP

4 CSP for CEC

4.1 CMOFs used as CSP

4.2 CCOFs used as CSP

4.3 Other materials used as CSP

5 CSP for other chromatography

6 Chiral separation mechanism

7 Conclusion and outlook

Key words: chiral porous materials, chiral stationery phase, high performance liquid chromatography, gas chromatography, capillary electrochromatography
Table 1 Separations of racemates on HPLC with chiral porous materials as CSP
No. Racemate α Rs ref
1 1-(1-naphthyl)ethanol 5.70 4.55 48
2 1-Phenyl-1-propanol 1.33 2.47 66
3 α-Methylbenzylamine 2.00 2.35 50
4 1,1'-Bi-2-naphthol 3.96 2.31 56
5 trans-stilbene oxide 7.24 4.09 51
6 DL-Mandelic acid 2.75 3.00 76
7 DL-malic acid 1.78 2.57 57
8 DL-Tyrosine 2.16 1.64 55
9 DL-Cysteine 2.46 1.91 55
10 DL-Phenylalanine 2.24 1.73 55
11 DL-Threonine 1.68 2.08 55
12 DL-Histidine 2.11 1.74 55
13 Benzoin 1.57 3.71 65
14 Zopiclone 6.74 2.24 56
15 Omeprazole 1.53 2.57 50
16 Ofloxacin 1.78 2.36 55
17 Chlorpheniramin 2.17 2.07 50
18 Naproxen 7.55 3.53 56
19 Ibuprofen 3.54 2.03 55
20 Praziquantel 3.29 2.14 56
Fig.1 Schematic demonstration for the preparation of D-His-ZIF-8@SiO2 core-shell microspheres[56]
Fig.2 Synthesis of the 3D chiral COFs[66]
Fig.3 The structure of CPOCs[86⇓⇓⇓~90]
Figure 4 Synthesis of MDI-β-CD-modified COF through the bottom-up strategy[120]
Table 2 Separations of racemates on chiral porous materials coated column of CEC
ref
Racemates		 Resolution (Rs)
115 116 118 119 120 121 122 123
1-(Naphthalen-1-yl)ethanol - - - - - - 1.13 -
Alprenlol - - - - - 1.11 - -
Arginine - - - - 2.85 - - -
Atenolol - - 2.15 - 2.97 - - -
Azelastine - - 2.1 - - - - -
Bendroflumethiazide - - - - - - 1.02 -
Benzoin - - - - - 3.35 0.63 1.71
Bisoprolol - - 1.88 - - - - -
Dns-DL-leucine - 2 - - - - - -
Dns-DL-phenylalanine - 2.24 - - - - - -
Dns-DL-serine - 1.4 - - - - - -
Dns-DL-threonine - 1.75 - - - - - -
Dns-DL-valine - 1.96 - - - - - -
Epinephrine 1.36 - - - - - - -
Esmolol - - 2.13 1.51 - - - -
Flavanone - - - - - - 0.56 -
Furoin - - - - - 1.42 1.18 1.35
Isoprenaline 1.61 - - - - - - -
Ketoprofen - - - - - - 1.34 -
Labetalol - - 0.58 - 1.95 - - -
Lysine - - - - 1.48 - - -
Mandelic acid - - - - - - 0.56 1.79
Metoprolol - - 1.58 1.53 - - - -
Ofloxacin - - - - - - 0.86 -
Omeprazole - - - - - - 2.23 -
Propranolol - - 1.73 1.57 - - - -
Salbutamol - - - 2.08 - - - -
Sotalol - - - 2.14 3.9 - - -
Synephrine 2.03 - - - - - - -
Terbutaline 2.09 - - - - - - -
Terbutaline - - - 1.7 - - - -
trans-stilbene oxide - - - - - - 1.58 -
Tryptophan - - - - 1.62 - - -
Tyrosine - - - - 1.81 - - -
Warfarin - - 1.57 - - - 0.66 -
Table 3 The CSPs and the main separation compounds introduced in this paper
Types Types of materials Name of CSPs Main separation analytes ref
HPLC CMOFs [Cd2(d-cam)3] ·2Hdma·4dma alcohol, naphthol, ketone, and base compounds 48
γ-CDMOF aromatic alcohol 49
[Zn(L-tyr)]n(L-tyrZn) alcohols, amines, ketones, ethers, organic acids 50
[Zn4(btc)2(Hbtc)(L-His)2(H2O)4]·1.5H2O
{[Zn2(L-trp)2(bpe)2(H2O)2] ·2H2O·2NO3}n
[Co2(L-Trp)(INT)2(H2O)2(ClO4)]
[Co2(sdba)((L-Trp)2]
[Co(L-Glu)(H2O)·H2O]∞
[Cu(H2O)2(S-TA)2]·6H2O ibuprofen, benzoin, furoin, thalidomide, trans-2,3-
Diphenyloxirane, 1-phenyl-ethan-1-ol, and flavanone		 51
[Zn(BDA)(bpe)]·2DMA sulfoxides, sec-alcohols and flavanones 52
[Zn(BDA)(bpa)]·2DMA
(R)-CuMOF-2 sec-alcohols, sulfoxides, epoxides, lactone, 1,3-dioxolan-2-one, and oxazolidinone 53
[Zn[(R)-1]2(NMF)2]·NMF sulfoxides, sec-alcohols, β-lactams, benzoins, flavanones and epoxides 54
[Nd3(D-cam)8(H2O)4Cl]n alcohols, amines, ketones, α-amino acids 55
D-his-ZIF-8@SiO2 alcohol, phenol, amine, ketone, and organic acid 56
Cu2((+)-Cam)2Dabco@SiO2 carboxylic acid, ketones and phenols 57
[Zn2(bdc)(L-lac)(dmf)](DMF) (±)-methyl phenyl sulfoxide 58
CCOFs BtaMth@SiO2 nitrotoluene, nitrochlorobenzene, beta-cypermethrin,
metconazole		 64
biomolecule⊂COF 1 DL-tryptophan, DL-leucine, DL-threonine, DL-lysine, DL-aspartic acid, ofloxacin, propranolol hydrochloride, metoprolol tartrate, alanyl glutamine, chlorpheniramine, benzoin 65
(R, R)-CCOF-6 1-phenyl-2-propanol, 1-phenyl-1-pentanol, 1-phenyl-1-propanol and 1-(4-bromophenyl)ethanol 66
CMSs HOCMS (C14-L-AlaA) alcohols, ketones, amines, aldehydes and organic acids 75
CMPs MP-CDPs 1-phenyl-1-propanol, 3-chloro-1-phenyl -1-propanol, mandelic acid, D/L-prolinol 76
GC CMOFs MIL-101(Al)-Xs (Xs=S-2-Ppa, R-Epo,
(+)-Ac-l-Ta, l-Pro, 1S-(+)-Cam)		 alcohols, amines, nitriles, esters and aldehydes 83
CMOM-3S aromatic alcohols and nitriles 84
PSO/CCS-3S aromatic alcohols, amines, nitriles, lactones, organic acid 85
CPOCs CC3-R/CC3-S chiral alcohols and amines 86
CC3-R chiral alcohols, diols, amines, alcohol amines, esters, ketones, ethers, halohydrocarbons, organic acids, amino acid methyl esters, and sulfoxides 87
CC10 chiral alcohols, esters, ketones, ethers, halohydrocarbons, epoxides, and organic acids 88
CC9 chiral alcohols, esters, ethers and epoxides 89
CC5 derivatized amino acids, alcohols, alcohol amines, esters, ethers, ketones, and epoxides 90
POC-1 alcohols, diols, esters, lactones, halohydrocarbons, ethers, epoxides, ketones and sulfoxides 91
CC9-OH alcohols, diols, halohydrocarbons, epoxides, esters, lactones, ketones, ethers, and organic acids 92
CC3R-OH chiral alcohols 93
CMOCs [Zn3L2] alcohols, diols, epoxides, ethers, halohydrocarbons, and esters 98
aMOP-A chiral alcohols, ethers, organic acids, amino acid derivatives 99
MOC-PA ethers, organic acids, ethers, amino acid derivatives 100
CCOFs CTpPa-1 (±)-1-phenylethanol; (±)-1-phenyl-1-propanol; (±)-limonene; (±)-methyl lactate 101
CMS HOCMS (C14-L-AlaA) chiral alcohols, aldehydes, esters, organic acids, epoxides, and amino acid derivatives 102
HOCMS (C14-L-Val) chiral alcohols, epoxides and amino acid derivatives 103
CMONs MON-TGC/MON-MSA/MON-NAC chiral alcohols 104
CEC CMOFs [Zn2(D-Cam)2(4,4'-bpy)]n DL-Phenylalanine, DL-Tyrosine 114
JLU-Liu23 epinephrine, isoprenaline, synephrine, terbutaline 115
Cu-SD@PD chiral Dns-amino acids 116
BSA@ZIF-8 epicatechin/catechin and salbutamol 117
CCOFs cellulase@poly(GMA-EDMA-SNW-1) (±)-atenolol,(±)-Metoprolol, (±)-bisoprolol,(±)-propranolol, (±)-esmolol,(±)-azelastine,(±)-warfarin, (±)-labetalol 118
β-CD COF (±)-sotalol, (±)-terbutaline, (±)-propranolol, (±)-Metoprolol, (±)-salbutamol and (±)-esmolol 119
MDI-β-CD-modified COF tryptophan, tyrosine, arginine, lysine, atenolol, labetalol, sotalol, and celiprolol 120
CPOCs CC3-R furoin, benzoin, alprenlol 121
CMOCs Zn3 L 2 1 Ofloxacin, Furoin, Benzoin, Omeprazole, Bendroflumethiazide 122
Zn3 L 2 2 Warfarin sodium, Ofloxacin, Mandelic acid, Ketoprofen
[Fe4 L 6 3](ClO4)8·Solvent Ofloxacin, 1-(Naphthalen-1-yl)ethanol, Flavanone, Trans-stilbene oxide
Zn3L2@poly(IL-co-EDMA) mandelic acid, benzoin, furoin 123
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