Natural and Artificial Chiral-Based Systems for Separation Applications

References

• Teixeira, J.; Tiritan, M. E.; Pinto, M. M.; Fernandes, C. Chiral Stationary Phases for Liquid Chromatography: Recent Developments. Molecules 2019, 24, 865. DOI: 10.3390/molecules24050865.
   PubMed Web of Science ®Google Scholar
• Shuang, Y.; Zhang, T.; Li, L. Preparation of a Stilbene Diamido-Bridged Bis(β-Cyclodextrin)-Bonded Chiral Stationary Phase for Enantioseparations of Drugs and Pesticides by High Performance Liquid Chromatography. J. Chromatogr. A 2020, 1614, 460702. DOI: 10.1016/j.chroma.2019.460702.
   PubMed Web of Science ®Google Scholar
• Dixit, S.; Park, J. Application of Antibiotics as Chiral Selectors for Capillary Electrophoretic Enantioseparation of Pharmaceuticals: A Review. Biomed. Chromatogr. 2014, 28, 10–26. DOI: 10.1002/bmc.2950.
   PubMed Web of Science ®Google Scholar
• Jiao, J.; Tan, C.; Li, Z.; Liu, Y.; Han, X.; Cui, Y. Design and Assembly of Chiral Coordination Cages for Asymmetric Sequential Reactions. J. Am. Chem. Soc. 2018, 140, 2251–2259. DOI: 10.1021/jacs.7b11679.
   PubMed Web of Science ®Google Scholar
• Vyviurska, O.; Zvrškovcová, H.; Špánik, I. Distribution of Enantiomers of Volatile Organic Compounds in Selected Fruit Distillates. Chirality 2017, 29, 14–18. DOI: 10.1002/chir.22669.
   PubMed Web of Science ®Google Scholar
• He, F.; Qian, Y. L.; Qian, M. C. Flavor and Chiral Stability of Lemon-Flavored Hard Tea during Storage. Food Chem. 2018, 239, 622–630. DOI: 10.1016/j.foodchem.2017.06.136.
   PubMed Web of Science ®Google Scholar
• Lehn, J. M. Supramolecular Chemistry—Scope and Perspectives Molecules, Supermolecules, and Molecular Devices (Nobel Lecture). Angew. Chem. Int. Ed. Engl. 1988, 27, 89–112. DOI: 10.1002/anie.198800891.
   Web of Science ®Google Scholar
• Kuhn, R.; Erni, F.; Bereuter, T.; Haeusler, J. Chiral Recognition and Enantiomeric Resolution Based on Host-Guest Complexation with Crown Ethers in Capillary Zone Electrophoresis. Anal. Chem. 1992, 64, 2815–2820. DOI: 10.1021/ac00046a026.
   Web of Science ®Google Scholar
• Ward, T. J.; Farris Iii, A. B. Chiral Separations Using the Macrocyclic Antibiotics: A Review. J. Chromatogr. A 2001, 906, 73–89. DOI: 10.1016/S0021-9673(00)00941-9.
   PubMed Web of Science ®Google Scholar
• Ilisz, I.; Grecso, N.; Forro, E.; Fulop, F.; Armstrong, D.; Peter, A. High-Performance Liquid Chromatographic Separation of Paclitaxel Intermediate Phenylisoserine Derivatives on Macrocyclic Glycopeptide and Cyclofructan-Based Chiral Stationary Phases. J. Pharm. Biomed. Anal. 2015, 114, 312–320. DOI: 10.1016/j.jpba.2015.06.007.
   PubMed Web of Science ®Google Scholar
• Ali, I.; Suhail, M.; Sanagi, M.; Aboul-Enein, H. Ionic Liquids in HPLC and CE: A Hope for Future. Crit. Rev. Anal. Chem. 2017, 47, 332–339. DOI: 10.1080/10408347.2017.1294047.
   PubMed Web of Science ®Google Scholar
• Catani, M.; Felletti, S.; Ismail, O. H.; Gasparrini, F.; Pasti, L.; Marchetti, N.; De Luca, C.; Costa, V.; Cavazzini, A. New Frontiers and Cutting Edge Applications in Ultra High Performance Liquid Chromatography through Latest Generation Superficially Porous Particles with Particular Emphasis to the Field of Chiral Separations. Anal. Bioanal. Chem. 2018, 410, 2457–2465. DOI: 10.1007/s00216-017-0842-4.
   PubMed Web of Science ®Google Scholar
• Gassmann, E.; Kuo, J. E.; Zare, R. N. Electrokinetic Separation of Chiral Compounds. Science 1985, 230, 813–814. DOI: 10.1126/science.230.4727.813.
   PubMed Web of Science ®Google Scholar
• Mallik, R.; Jiang, T.; Hage, D. High-Performance Affinity Monolith Chromatography: Development and Evaluation of Human Serum Albumin Columns. Anal. Chem. 2004, 76, 7013–7022. DOI: 10.1021/ac049001q.
   PubMed Web of Science ®Google Scholar
• Prier, C. K.; Zhang, R. K.; Buller, A. R.; Brinkmann-Chen, S.; Arnold, F. Enantioselective, Intermolecular Benzylic C–H Amination Catalysed by an Engineered Iron-Haem Enzyme. Nat. Chem. 2017, 9, 629–634. DOI: 10.1038/nchem.2783.
   PubMed Web of Science ®Google Scholar
• Kim, C. R.; Uemura, T.; Kitagawa, S. Inorganic Nanoparticles in Porous Coordination Polymers. Chem. Soc. Rev. 2016, 45, 3828–3845. DOI: 10.1039/c5cs00940e.
   PubMed Web of Science ®Google Scholar
• Yang, Q. H.; Xu, Q.; Jiang, H. L. Metal–Organic Frameworks Meet Metal Nanoparticles: Synergistic Effect for Enhanced Catalysis. Chem. Soc. Rev. 2017, 46, 4774–4808. DOI: 10.1039/C6CS00724D.
   PubMed Web of Science ®Google Scholar
• Kotake, M.; Sakan, T.; Nakamura, N.; Senoh, S. Resolution into Optical Isomers of Some Amino Acids by Paper Chromatography. J. Am. Chem. Soc. 1951, 73, 2973–2974. DOI: 10.1021/ja01150a548.
   Web of Science ®Google Scholar
• Hesse, G.; Hagel, R. Über Inclusions-Chromatographie und in neues Retentionsprinzip für benzolderivate. Chromatographia 1976, 9, 62–68. DOI: 10.1007/BF02269220.
   Google Scholar
• Ikai, T.; Yamamoto, C.; Kamigaito, M.; Okamoto, Y. Immobilized-Type Chiral Packing Materials for HPLC Based on Polysaccharide Derivatives. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2008, 875, 2–11. DOI: 10.1016/j.jchromb.2008.04.047.
   PubMed Web of Science ®Google Scholar
• Yamamoto, C.; Yashima, E.; Okamoto, Y. Structural Analysis of Amylose Tris(3,5-Dimethylphenylcarbamate) by NMR Relevant to Its Chiral Recognition Mechanism in HPLC. J. Am. Chem. Soc. 2002, 124, 12583–12589. DOI: 10.1021/ja020828g.
   PubMed Web of Science ®Google Scholar
• Wang, X.; House, D. W.; Oroskar, P. A.; Oroskar, A.; Oroskar, A.; Jameson, C. J.; Murad, S. Molecular Dynamics Simulations of the Chiral Recognition Mechanism for a Polysaccharide Chiral Stationary Phase in Enantiomeric Chromatographic Separations. Mol. Phys. 2019, 117, 3569–3588. DOI: 10.1080/00268976.2019.1647360.
   Web of Science ®Google Scholar
• Tang, S. W.; Jin, Z. L.; Sun, B. S.; Wang, F.; Tang, W. Y. Preparation and Evaluation of Regioselectively Substituted Amylose Derivatives for Chiral Separations. Chirality 2017, 29, 512–521. DOI: 10.1002/chir.22720.
   PubMed Web of Science ®Google Scholar
• Shen, J.; Wang, F.; Bi, W.; Liu, B.; Liu, S.; Okamoto, Y. Synthesis of Cellulose Carbamates Bearing Regioselective Substituents at 2,3- and 6-Positions for Efficient Chromatographic Enantioseparation. J. Chromatogr. A 2018, 1572, 54–61. DOI: 10.1016/j.chroma.2018.08.032.
   PubMed Web of Science ®Google Scholar
• Dai, X.; Bi, W. Y.; Sun, M. C.; Wang, F.; Shen, J.; Okamoto, Y. Chiral Recognition Ability of Amylose Derivatives Bearing Regioselectively Different Carbamate Pendants at 2, 3-and 6-Positions. Carbohydr. Polym. 2019, 218, 30–36. DOI: 10.1016/j.carbpol.2019.03.052.
   PubMed Web of Science ®Google Scholar
• Ogasawara, M.; Enomoto, Y.; Uryu, M.; Yang, X. C.; Kataoka, A.; Ohnishi, A. Application of Polysaccharide-Based Chiral Hplc Columns for Separation of Nonenantiomeric Isomeric Mixtures of Organometallic Compounds. Organometallics 2019, 38, 512–518. DOI: 10.1021/acs.organomet.8b00819.
   Web of Science ®Google Scholar
• Sadutto, D.; Ferretti, R.; Zanitti, L.; Casulli, A.; Cirilli, R. Analytical and Semipreparative High Performance Liquid Chromatography Enantioseparation of Bicalutamide and Its Chiral Impurities on an Immobilized Polysaccharide-Based Chiral Stationary Phase. J. Chromatogr. A 2016, 1445, 166–171. DOI: 10.1016/j.chroma.2016.04.011.
   PubMed Web of Science ®Google Scholar
• Zeng, Q. L.; Wen, Q.; Xiang, Y.; Zhang, L. Chromatographic Enantioseparation of Chiral Sulfinamide Derivatives on Polysaccharide-Based Chiral Stationary Phases. J. Chromatogr. A 2018, 1571, 240–244. DOI: 10.1016/j.chroma.2018.08.010.
   PubMed Web of Science ®Google Scholar
• Rane, V. P.; Ahirrao, V. K.; Patil, K. R.; Jadhav, A. K.; More, K. B.; Yeole, R. D. Liquid Chromatographic Separation and Thermodynamic Investigation of Ethyl Nipecotate Enantiomers on Immobilized Amylose-Based Chiral Stationary Phase. J. Chromatogr. Sci. 2019, 57, 815–820. DOI: 10.1093/chromsci/bmz065.
   PubMed Web of Science ®Google Scholar
• Armstrong, D. W.; Tang, Y.; Chen, S.; Zhou, Y.; Bagwill, C.; Chen, J. R. Macrocyclic Antibiotics as a New Class of Chiral Selectors for Liquid Chromatography. Anal. Chem. 1994, 66, 1473–1484. DOI: 10.1021/ac00081a019.
   Web of Science ®Google Scholar
• Armstrong, D. W.; Rundlett, K. L.; Chen, J. R. Evaluation of the Macrocyclic Antibiotic Vancomycin as a Chiral Selector for Capillary Electrophoresis. Chirality 1994, 6, 496–509. DOI: 10.1002/chir.530060609.
   PubMed Web of Science ®Google Scholar
• Cardoso, P. A.; César, I. C. Chiral Method Development Strategies for Hplc Using Macrocyclic Glycopeptide-Based Stationary Phases. Chromatographia 2018, 81, 841–850. DOI: 10.1002/chir.20600.
   Web of Science ®Google Scholar
• Berthod, A. Chiral Recognition Mechanisms with Macrocyclic Glycopeptide Selectors. Chirality 2009, 21, 167–175. DOI: 10.1002/chir.20600.
   PubMed Web of Science ®Google Scholar
• Phyo, Y.; Cravo, S.; Palmeira, A.; Tiritan, M.; Kijjoa, A.; Pinto, M.; Fernandes, C. Enantiomeric Resolution and Docking Studies of Chiral Xanthonic Derivatives on Chirobiotic Columns. Molecules 2018, 23, 142. DOI: 10.3390/molecules23010142.
   PubMed Web of Science ®Google Scholar
• Ali, I.; Suhail, M.; Asnin, L. Chiral Separation and Modeling of Quinolones on Teicoplanin Macrocyclic Glycopeptide Antibiotics CSP. Chirality 2018, 30, 1304–1311. DOI: 10.1002/chir.23024.
   PubMed Web of Science ®Google Scholar
• Ismail, O. H.; Antonelli, M.; Ciogli, A.; De Martino, M.; Catani, M.; Villani, C.; Cavazzini, A.; Ye, M.; Bell, D. S.; Gasparrini, F. Direct Analysis of Chiral Active Pharmaceutical Ingredients and Their Counterions by Ultra High Performance Liquid Chromatography with Macrocyclic Glycopeptide-Based Chiral Stationary Phases. J. Chromatogr. A 2018, 1576, 42–50. DOI: 10.1016/j.chroma.2018.09.029.
   PubMed Web of Science ®Google Scholar
• Jang, M. G.; Jang, M. D.; Park, J. H. Doxycycline as a New Chiral Selector in Capillary Electrophoresis. J. Chromatogr. A 2017, 1508, 176–181. DOI: 10.1016/j.chroma.2017.06.019.
   PubMed Web of Science ®Google Scholar
• Zheng, Y.; Wang, X.; Ji, Y. B. Monoliths with Proteins as Chiral Selectors for Enantiomer Separation. Talanta 2012, 91, 7–17. DOI: 10.1016/j.talanta.2012.01.039.
   PubMed Web of Science ®Google Scholar
• Tan, H. L.; Chen, Q. B.; Chen, T. T.; Liu, H. L. Effects of Rigid Conjugated Groups: Toward Improving Enantioseparation Performances of Chiral Porous Organic Polymers. ACS Appl. Mater. Interfaces 2019, 11, 37156–37162. DOI: 10.1021/acsami.9b14144.
   PubMed Web of Science ®Google Scholar
• Septiana, D.; Angga, S. C.; Amalia, S.; Iftitah, E. D.; Sabarudin, A. Modification of Monolithic Stationary Phase Using Human Serum Albumin as Chiral Separation. AIP Conf. Proc. 2018, 2021, 050004. DOI: 10.1063/1.5062754.
   Google Scholar
• Kan, S. B. J.; Lewis, R. D.; Chen, K.; Arnold, F. H. Directed Evolution of Cytochrome c for Carbon-Silicon Bond Formation: Bringing Silicon to Life. Science 2016, 354, 1048–1051. DOI: 10.1126/science.aah6219.
   PubMed Web of Science ®Google Scholar
• Ji, L. K.; Sang, Y. T.; Ouyang, G. H.; Yang, D.; Duan, P. F.; Jiang, Y. Q.; Liu, M. H. Cooperative Chirality and Sequential Energy Transfer in a Supramolecular Light-Harvesting Nanotube. Angew. Chem. Int. Ed. 2019, 58, 844–848. DOI: 10.1002/anie.201812642.
   PubMed Web of Science ®Google Scholar
• Scriba, G. K. E. Chiral Recognition Mechanisms in Analytical Separation Sciences. Chromatographia 2012, 75, 815–838. DOI: 10.1007/s10337-012-2261-1.
   Web of Science ®Google Scholar
• Armstrong, D. W.; DeMond, W. Cyclodextrin Bonded Phases for the Liquid Chromatographic Separation of Optical, Geometrical, and Structural Isomers. J. Chromatogr. Sci. 1984, 22, 411–415. DOI: 10.1093/chromsci/22.9.411.
   Web of Science ®Google Scholar
• Wang, S. Y.; Li, L.; Xiao, Y.; Wang, Y. Recent Advances in Cyclodextrins-Based Chiralrecognizing Platforms. TrAC-Trend. Anal. Chem. 2019, 121, 115691. DOI: 10.1016/j.trac.2019.115691.
   Web of Science ®Google Scholar
• Rahim, N. Y.; Tay, K. S.; Mohamad, S. Chromatographic and Spectroscopic Studies on β-Cyclodextrin Functionalized Ionic Liquid as Chiral Stationary Phase: enantioseparation of Flavonoids. Chromatographia 2016, 79, 1445–1455. DOI: 10.1007/s10337-016-3169-y.
   Web of Science ®Google Scholar
• Zhao, Y.; Wang, J. L.; Liu, Y. R.; Jiang, Z.; Song, Y. B.; Guo, X. J. Enantioseparation Using Carboxymethyl-6-(4-Methoxybenzylamino)-β-Cyclodextrin as a Chiral Selector by Capillary Electrophoresis and Molecular Modeling Study of the Recognition Mechanism. New J. Chem. 2020, 44, 958–972. DOI: 10.1039/C9NJ04771A.
   Web of Science ®Google Scholar
• Yuan, L. M.; Ma, W.; Xu, M.; Zhao, H. L.; Li, Y. Y.; Wang, R. L.; Duan, A. H.; Ai, P.; Chen, X. X. Optical Resolution and Mechanism Using Enantioselective Cellulose, Sodium Alginate and Hydroxypropyl-β-Cyclodextrin Membranes. Chirality 2017, 29, 315–324. DOI: 10.1002/chir.22693.
   PubMed Web of Science ®Google Scholar
• Guo, J.; Wang, Q.; Xu, D.; Crommen, J.; Jiang, Z. Recent Advances in Preparation and Applications of Monolithic Chiral Stationary Phases. TrAC-Trend. Anal. Chem. 2020, 123, 115774. DOI: 10.1016/j.trac.2019.115774.
   Web of Science ®Google Scholar
• Li, Q.; Li, Y. Y.; Zhu, N.; Gao, Z. X.; Li, T. J.; Zhou, T.; Ma, Y. L. Preparation of Cyclodextrin Type Stationary Phase Based on Graphene Oxide and Its Application in Enantioseparation and Hydrophilic Interaction Chromatography. Chin. J. Anal. Chem. 2018, 46, 1455–1463. DOI: 10.1016/S1872-2040(18)61111-9.
   Web of Science ®Google Scholar
• Adhikari, S.; Lee, W. Chiral Separation Using Chiral Crown Ethers as Chiral Selectors in Chirotechnology. J. Pharm. Investig. 2018, 48, 225–231. DOI: 10.1007/s40005-017-0348-2.
   Google Scholar
• Kuhn, R. Enantiomeric Separation by Capillary Electrophoresis Using a Crown Ether as Chiral Selector. Electrophoresis 1999, 20, 2605–2613. DOI: 10.1002/(SICI)1522-2683(19990901)20:13 < 2605::AID-ELPS2605 > 3.0.CO;2-M.
   PubMed Web of Science ®Google Scholar
• Lv, L. Q.; Bu, Z. S.; Sun, W. Y.; Wang, C. Y.; Xu, C.; Tong, S. Q. Application of pH-Zone-Refining Countercurrent Chromatography in the Chiral Separation of Two β-Adrenergic Blocking Agents. J. Sep. Sci. 2018, 41, 1433–1441. DOI: 10.1002/jssc.201701181.
   PubMed Web of Science ®Google Scholar
• Bang, E.; Jung, J. W.; Lee, W.; Lee, D. W.; Lee, W. Chiral Recognition of (18-Crown-6)-Tetracarboxylic Acid as a Chiral Selector Determined by NMR Spectroscopy. J. Chem. Soc. Perkin. Trans. 2. 2001, 2, 1685–1692. DOI: 10.1039/b102026i.
   Google Scholar
• Mohammadzadeh Kakhki, R.; Assadi, H. Capillary Electrophoresis Analysis Based on Crown Ethers. J. Incl. Phenom. Macrocycl. Chem. 2015, 81, 1–12. DOI: 10.1007/s10847-014-0419-1.
   Web of Science ®Google Scholar
• Hyun, M. H. Liquid Chromatographic Enantioseparations on Crown Ether-Based Chiral Stationary Phases. J. Chromatogr. A 2016, 1467, 19–32. DOI: 10.1016/j.chroma.2016.07.049.
   PubMed Web of Science ®Google Scholar
• Lee, S.; Kim, S. J.; Bang, E.; Na, Y. C. Chiral Separation of Intact Amino Acids by Capillary Electrophoresis-Mass Spectrometry Employing a Partial Filling Technique with a Crown Ether Carboxylic Acid. J. Chromatogr. A 2019, 1586, 128–138. DOI: 10.1016/j.chroma.2018.12.001.
   PubMed Web of Science ®Google Scholar
• Liu, L. Z.; He, C. H.; Yang, L.; Huang, Y.; Wu, Q.; Duan, W. G.; Wang, H. S.; Pan, Y. M. Novel C1-Symmetric Chiral Crown Ethers Bearing Rosin Acids Groups: Synthesis and Enantiomeric Recognition for Ammonium Salts. Tetrahedron 2014, 70, 9545–9553. 10.050. DOI: 10.1016/j.tet.2014.
   Web of Science ®Google Scholar
• Li, B.; Wen, H. M.; Cui, Y. J.; Zhou, W.; Qian, G. D.; Chen, B. L. Emerging Multifunctional Metal–Organic Framework Materials. Adv. Mater. 2016, 28, 8819–8860. DOI: 10.1002/adma.201601133.
   PubMed Web of Science ®Google Scholar
• Schurig, V.; Betschinger, F. Metal-Mediated Enantioselective Access to Unfunctionalized Aliphatic Oxiranes: Prochiral and Chiral Recognition. Chem. Rev. 1992, 92, 873–888. DOI: 10.1021/cr00013a006.
   Web of Science ®Google Scholar
• Gus’kov, V. Y.; Maistrenko, V. N. New Chiral Stationary Phases: Preparation, Properties, and Applications in Gas Chromatography. J. Anal. Chem. 2018, 73, 937–945. DOI: 10.1134/S1061934818100027.
   Web of Science ®Google Scholar
• Schurig, V. Resolution of a Chiral Olefin by Complexation Chromatography on an Optically Active Rhodium(I) Complex. Angew. Chem. Int. Ed. Engl. 1977, 16, 110–110. DOI: 10.1002/anie.197701101.
   Web of Science ®Google Scholar
• Janczak, J.; Prochowicz, D.; Lewiński, J.; Fairen-Jimenez, D.; Bereta, T.; Lisowski, J. Trinuclear Cage-like ZnII Macrocyclic Complexes: Enantiomeric Recognition and Gas Adsorption Properties. Chemistry 2016, 22, 598–609. DOI: 10.1002/chem.201503479.
   PubMed Web of Science ®Google Scholar
• Xie, S. M.; Fu, N.; Li, L.; Yuan, B. Y.; Zhang, J. H.; Li, Y. X.; Yuan, L. M. Homochiral Metal–Organic Cage for Gas Chromatographic Separations. Anal. Chem. 2018, 90, 9182–9188. DOI: 10.1021/acs.analchem.8b01670.
   PubMed Web of Science ®Google Scholar
• Xie, S. M.; Chen, X. X.; Zhang, J. H.; Yuan, L. M. Gas Chromatographic Separation of Enantiomers on Novel Chiral Stationary Phases. TrAC-Trend. Anal. Chem. 2020, 124, 115808. DOI: 10.1016/j.trac.2020.115808.
   Web of Science ®Google Scholar
• Zhang, J. Y.; Chen, J. X.; Peng, S.; Peng, S. Y.; Zhang, Z. Z.; Tong, Y. X.; Miller, P. W.; Yan, X. P. Emerging Porous Materials in Confined Spaces: From Chromatographic Applications to Flow Chemistry. Chem. Soc. Rev. 2019, 48, 2566–2595. DOI: 10.1039/C8CS00657A.
   PubMed Web of Science ®Google Scholar
• Suchandra, B.; Khan, M.; Li, X. F.; Zhu, Q. L.; Wu, X. Recent Progress in Asymmetric Catalysis and Chromatographic Separation by Chiral Metal–Organic. Catalysts 2018, 8, 120. DOI: 10.3390/catal8030120.
   Web of Science ®Google Scholar
• Gupta, A. K.; De, D.; Katoch, R.; Garg, A.; Bharadwaj, P. K. Synthesis of a nbO Type Homochiral Cu(II) Metal–Organic Framework: Ferroelectric Behavior and Heterogeneous Catalysis of Three-Component Coupling and Pechmann Reactions. Inorg. Chem. 2017, 56, 4697–4705. DOI: 10.1021/acs.inorgchem.7b00342.
   Web of Science ®Google Scholar
• Xia, Q. C.; Li, Z. J.; Tan, C. X.; Liu, Y.; Gong, W.; Cui, Y. Multivariate Metal–Organic Frameworks as Multifunctional Heterogeneous Asymmetric Catalysts for Sequential Reactions. J. Am. Chem. Soc. 2017, 139, 8259–8266. DOI: 10.1021/jacs.7b03113.
   PubMed Web of Science ®Google Scholar
• Hou, X.; Xu, T.; Wang, Y.; Liu, S.; Tong, J.; Liu, B. Superficial Chiral Etching on Achiral Metal-Organic Framework for Enantioselective Sorption. ACS Appl. Mater. Interfaces 2017, 9, 32264–32269. DOI: 10.1021/acsami.7b10147.
   PubMed Web of Science ®Google Scholar
• Chen, J.; Chen, X.; Zhang, Z.; Bao, Z.; Xing, H.; Yang, Q.; Ren, Q. MIL-101(Cr) as a Synergistic Catalyst for the Reduction of Imines with Trichlorosilane. Mol. Catal. 2018, 445, 163–169. DOI: 10.1016/j.mcat.2017.11.012.
   Google Scholar
• Chen, B. L.; Liang, C. D.; Yang, J.; Contreras, D. S.; Clancy, Y. L.; Lobkovsky, E. B.; Yaghi, O. M.; Dai, S. A Microporous Metal–Organic Framework for Gas-Chromatographic Separation of Alkanes. Angew. Chem. Int. Ed. Engl. 2006, 45, 1390–1393. DOI: 10.1002/anie.200502844.
   PubMed Web of Science ®Google Scholar
• Xie, S. M.; Zhang, Z. J.; Wang, Z. Y.; Yuan, L. M. Chiral Metal–Organic Frameworks for High-Resolution Gas Chromatographic Separations. J. Am. Chem. Soc. 2011, 133, 11892–11895. DOI: 10.1021/ja2044453.
   PubMed Web of Science ®Google Scholar
• Li, L.; Xie, S. M.; Zhang, J. H.; Chen, L.; Zhu, P. J.; Yuan, L. M. A Gas Chromatographic Stationary of Homochiral Metal-Peptide Framework Material and Its Applications. Chem. Res. Chin. Univ. 2017, 33, 24–30. DOI: 10.1007/s40242-017-6270-3.
   Web of Science ®Google Scholar
• Brandt, K.; Dötterl, S.; Fuchs, R.; Navarro, D. M. d A. F.; Machado, I. C. S.; Dobler, D.; Reiser, O.; Ayasse, M.; Milet-Pinheiro, P. Subtle Chemical Variations with Strong Ecological Significance: Stereoselective Responses of Male Orchid Bees to Stereoisomers of Carvone Epoxide. J. Chem. Ecol. 2019, 45, 464–473. DOI: 10.1007/s10886-019-01072-6.
   PubMed Web of Science ®Google Scholar
• Gumustas, M.; Ozkan, S. A.; Chankvetadze, B. Analytical and Preparative Scale Separation of Enantiomers of Chiral Drugs by Chromatography and Related Methods. Curr. Med. Chem. 2018, 25, 4152–4188. DOI: 10.2174/0929867325666180129094955.
   PubMed Web of Science ®Google Scholar
• Waller, P. J.; Gándara, F.; Yaghi, O. M. Chemistry of Covalent Organic Frameworks. Acc. Chem. Res. 2015, 48, 3053–3063. DOI: 10.1021/acs.accounts.5b00369.
   PubMed Web of Science ®Google Scholar
• Yang, C. X.; Liu, C.; Cao, Y. M.; Yan, X. P. Facile Room-Temperature Solution-Phase Synthesis of a Spherical Covalent Organic Framework for High-Resolution Chromatographic Separation. Chem. Commun. (Camb.) 2015, 51, 12254–12257. DOI: 10.1039/C5CC03413B.
   PubMed Web of Science ®Google Scholar
• Qian, H. L.; Yang, C. X.; Yan, X. P. Bottom-up Synthesis of Chiral Covalent Organic Frameworks and Their Bound Capillaries for Chiral Separation. Nat. Commun. 2016, 7, 12104. DOI: 10.1038/ncomms12104.
   PubMed Web of Science ®Google Scholar
• Liu, L. H.; Yang, C. X.; Yan, X. P. Methacrylate-Bonded Covalent-Organic Framework Monolithic Columns for High Performance Liquid Chromatography. J. Chromatogr. A 2017, 1479, 137–144. DOI: 10.1016/j.chroma.2016.12.004.
   PubMed Web of Science ®Google Scholar
• Wang, S. L.; Zhang, L. Y.; Xiao, R. L.; Chen, H. H.; Chu, Z. Y.; Zhang, W. B.; Liu, F. Fabrication of SiO2@COF5 Microspheres and Its Application in High Performance Liquid Chromatography. Anal. Methods 2018, 10, 1968–1976. DOI: 10.1039/C8AY00459E.
   Web of Science ®Google Scholar
• Han, X.; Huang, J. J.; Yuan, C.; Liu, Y.; Cui, Y. Chiral 3D Covalent Organic Frameworks for High Performance Liquid Chromatographic Enantioseparation. J. Am. Chem. Soc. 2018, 140, 892–895. DOI: 10.1021/jacs.7b12110.
   PubMed Web of Science ®Google Scholar
• Chen, L.; Gao, J.; Wu, Q.; Li, H.; Dong, S.; Shi, X.; Zhao, L. Preparation and Performance of a Novel Multi-Mode COF-300@SiO2 Chromatographic Stationary Phase. Eur. Polym. J. 2019, 116, 9–19. DOI: 10.1016/j.eurpolymj.2019.04.002.
   Web of Science ®Google Scholar
• Huang, X. L.; Lan, H. H.; Yan, Y. L.; Chen, G.; He, Z. H.; Zhang, K.; Cai, S. L.; Zheng, S. R.; Fan, J.; Zhang, W. G. Fabrication of a Hydrazone-Linked Covalent Organic Framework-Bound Capillary Column for Gas Chromatography Separation. Sep. Sci. Plus. 2019, 2, 120–128. DOI: 10.1002/sscp.201800146.
   Web of Science ®Google Scholar
• Dixit, S.; Park, J. H. Enantioseparation of Basic Chiral Drugs on a Carbamoylated Erythromycin-Zirconia Hybrid Monolith Using Capillary Electrochromatography. J. Chromatogr. A 2015, 1416, 129–136. DOI: 10.1016/j.chroma.2015.09.018.
   PubMed Web of Science ®Google Scholar
• Holst, J. R.; Trewin, A.; Cooper, A. I. Porous Organic Molecules. Nat. Chem. 2010, 2, 915–920. DOI: 10.1038/nchem.873.
   PubMed Web of Science ®Google Scholar
• Zhang, J. H.; Xie, S. M.; Zi, M.; Yuan, L. M. Recent Advances of Application of Porous Molecular Cages for Enantioselective Recognition and Separation. J. Sep. Sci. 2020, 43, 134–149. DOI: 10.1002/jssc.201900762.
   PubMed Web of Science ®Google Scholar
• Quan, M. L. C.; Cram, D. J. Constrictive Binding of Large Guests by a Hemicarcerand Containing Four Portals. J. Am. Chem. Soc. 1991, 113, 2754–2755. DOI: 10.1021/ja00007a060.
   Web of Science ®Google Scholar
• Zhang, J. H.; Xie, S. M.; Chen, L.; Wang, B. J.; He, P. G.; Yuan, L. M. Homochiral Porous Organic Cage with High Selectivity for the Separation of Racemates in Gas Chromatography. Anal. Chem. 2015, 87, 7817–7824. DOI: 10.1021/acs.analchem.5b01512.
   PubMed Web of Science ®Google Scholar
• Saroj, S.; Rajput, S. J. Composite Smart Mesoporous Silica Nanoparticles as Promising Therapeutic and Diagnostic Candidates: Recent Trends and Applications. J. Drug Deliv. Sci. Technol. 2018, 44, 349–365. DOI: 10.1016/j.jddst.2018.01.014.
   Web of Science ®Google Scholar
• Che, S. N.; Liu, Z.; Ohsuna, T.; Sakamoto, K.; Terasaki, O.; Tatsumi, T. Synthesis and Characterization of Chiral Mesoporous Silica. Nature 2004, 429, 281–284. DOI: 10.1038/nature02529.
   PubMed Web of Science ®Google Scholar
• Trewyn, B. G.; Whitman, C. M.; Lin, V. S. Y. Morphological Control of Room-Temperature Ionic Liquid Templated Mesoporous Silica Nanoparticles for Controlled Release of Antibacterial Agents. Nano Lett. 2004, 4, 2139–2143. [Database] DOI: 10.1021/nl048774r.
   Web of Science ®Google Scholar
• He, Y. Y.; Pu, Q.; Zhang, J. H.; Xie, S. M.; Chen, X. X.; Yuan, L. M. Chiral Inorganic Mesoporous Materials Used as the Stationary Phase in GC. Sep. Sci. Plus. 2019, 2, 432–439. DOI: 10.1002/sscp.201900067.
   Web of Science ®Google Scholar
• He, Y. Y.; Zhang, J. H.; Pu, Q.; Xie, S. M.; Li, Y. X.; Luo, L.; Chen, X. X.; Yuan, L. M. A Novel Chiral Inorganic Mesoporous Silica Used as a Stationary Phase in GC. Chirality 2019, 31, 1053–1059. DOI: 10.1002/chir.23134.
   PubMed Web of Science ®Google Scholar
• Pirkle, W.; House, D. Chiral High-Performance Liquid Chromatographic Stationary Phases. 1. Separation of the Enantiomers of Sulfoxides, Amines, Amino Acids, Alcohols, Hydroxy Acids, Lactones, and Mercaptans. J. Org. Chem. 1979, 44, 1957–1960. DOI: 10.1016/s0021-9673(00)00917-1.
   Web of Science ®Google Scholar
• Welch, C. J. Evolution of Chiral Stationary Phase Design in the Pirkle Laboratories. J. Chromatogr. A 1994, 666, 3–26. DOI: 10.1016/0021-9673(94)80367-6.
   Web of Science ®Google Scholar
• Pirkle, W. H. The Nonequivalence of Physical Properties of Enantiomers in Optically Active Solvents. differences in Nuclear Magnetic Resonance Spectra. I. J. Am. Chem. Soc. 1966, 88, 1837–1837. DOI: 10.1021/ja00960a060.
   PubMed Web of Science ®Google Scholar
• Scriba, G. K. E. Chiral Recognition in Separation Sciences. Part II: Macrocyclic Glycopeptide, Donor-Acceptor, Ion-Exchange, Ligand-Exchange and Micellar Selectors. TrAC-Trend. Anal. Chem. 2019, 119, 115628. DOI: 10.1016/j.trac.2019.115628.
   Web of Science ®Google Scholar
• Scriba, G. K. E. Chiral Recognition in Separation Science - An Update. J. Chromatogr. A 2016, 1467, 56–78. DOI: 10.1016/j.chroma.2016.05.061.
   PubMed Web of Science ®Google Scholar
• Fernandes, C.; Tiritan, M. E.; Pinto, M. Small Molecules as Chromatographic Tools for HPLC Enantiomeric Resolution: Pirkle-Type Chiral Stationary Phases Evolution. Chromatographia 2013, 76, 871–897. DOI: 10.1007/s10337-013-2469-8.
   Web of Science ®Google Scholar
• Fernandes, C.; Phyo, Y. Z.; Silva, A. S.; Tiritan, M. E.; Kijjoa, A.; Pinto, M. M. Chiral Stationary Phases Based on Small Molecules: An Update of the Last 17 Years. Sep. Purif. Rev. 2018, 47, 89–123. DOI: 10.1080/15422119.2017.1326939.
   Web of Science ®Google Scholar
• Sabia, R.; De Martino, M.; Cavazzini, A.; Villani, C. Dynamic Behavior of Clobazam on High-Performance Liquid Chromatography Chiral Stationary Phases. Chirality 2016, 28, 17–21. DOI: 10.1002/chir.22542.
   PubMed Web of Science ®Google Scholar
• Knežević, A.; Novak, J.; Vinković, V. New Brush-Type Chiral Stationary Phases for Enantioseparation of Pharmaceutical Drugs. Molecules 2019, 24, 823. DOI: 10.3390/molecules24040823.
   PubMed Web of Science ®Google Scholar
• Çakmak, R.; Ercan, S.; Sünkür, M.; Yılmaz, H.; Topal, G. Design, Preparation and Application of a Pirkle-Type Chiral Stationary Phase for Enantioseparation of Some Racemic Organic Acids and Molecular Dynamics Studies. Org. Commun. 2017, 10, 216–227. DOI: 10.25135/acg.oc.25.17.07.037.
   Web of Science ®Google Scholar
• Sung, J. Y.; Choi, S. H.; Hyun, M. H. Preparation of a New Chiral Stationary Phase Based on Macrocyclic Amide Chiral Selector for the Liquid Chromatographic Chiral Separations. Chirality 2016, 28, 253–258. DOI: 10.1002/chir.22569.
   PubMed Web of Science ®Google Scholar
• Yu, J.; Armstrong, D. W.; Ryoo, J. J. Synthesis of New C3 Symmetric Amino Acid‐and Aminoalcohol‐Containing Chiral Stationary Phases and Application to HPLC Enantioseparations. Chirality 2018, 30, 74–84. DOI: 10.1002/chir.22766.
   PubMed Web of Science ®Google Scholar
• Yu, J.; Ryoo, D. H.; Lee, J. M.; Ryoo, J. J. Synthesis and Application of C2 and C3 Symmetric (R)‐Phenylglycinol‐Derived Chiral Stationary Phases. Chirality 2016, 28, 186–191. DOI: 10.1002/chir.22572.
   PubMed Web of Science ®Google Scholar
• Poole, C. F.; Lenca, N. Gas Chromatography on Wall-Coated Open-Tubular Columns with Ionic Liquid Stationary Phases. J. Chromatogr. A 2014, 1357, 87–109. DOI: 10.1016/j.chroma.2014.03.029.
   PubMed Web of Science ®Google Scholar
• Kimaru, I. W.; Morris, L.; Vassiliou, J.; Savage, N. Synthesis and Evaluation of l-Phenylalanine Ester-Based Chiral Ionic Liquids for GC Stationary Phase Ability. J. Mol. Liq. 2017, 237, 193–200. DOI: 10.1016/j.molliq.2017.04.079.
   Web of Science ®Google Scholar
• Kapnissi-Christodoulou, C. P.; Stavrou, I. J.; Mavroudi, M. C. Chiral Ionic Liquids in Chromatographic and Electrophoretic Separations. J. Chromatogr. A 2014, 1363, 2–10. DOI: 10.1016/j.chroma.2014.05.059.
   PubMed Web of Science ®Google Scholar
• Xu, H.; Feng, Z. J.; Du, Y. X. Synthesis, Application and Molecular Modeling Study of Ionic Liquid Functionalized Lactobionic Acid, 3-Methyl-1-(3-Sulfopropyl)-1H-Imidazol-3-Ium Lactobionate, as a Chiral Selector in Capillary Electrophoresis. Analyst 2020, 145, 1025–1032. DOI: 10.1039/C9AN02009H.
   PubMed Web of Science ®Google Scholar
• Sedghamiz, T.; Bahrami, M. Molecular Dynamics Simulation Study of the Effect of Single-Walled Carbon Nanotube on the Enantioseparation Ability of a Chiral Ionic Liquid. J. Mol. Liq. 2020, 304, 112769. DOI: 10.1016/j.molliq.2020.112769.
   Web of Science ®Google Scholar
• Sedghamiz, T.; Ghalami, F.; Sedghamiz, E.; Bahrami, M. Chiral Recognition of Propranolol Enantiomers by Chiral Ionic Liquid: A Quantum Chemical Calculation Analysis. Comput. Theor. Chem. 2018, 1140, 38–48. DOI: 10.1016/j.comptc.2018.07.017.
   Web of Science ®Google Scholar
• Xu, G. F.; Du, Y. X.; Du, F.; Chen, J. Q.; Yu, T.; Zhang, Q.; Zhang, J. J.; Du, S. J.; Feng, Z. J. Establishment and Evaluation of the Novel tetramethylammonium-L-Hydroxyproline Chiral Ionic Liquid Synergistic System Based on Clindamycin Phosphate for Enantioseparation by Capillary Electrophoresis. Chirality 2015, 27, 598–604. DOI: 10.1002/chir.22463.
   PubMed Web of Science ®Google Scholar
• Zhu, X. Q.; Chen, C.; Chen, J. Q.; Xu, G. F.; Du, Y. X.; Ma, X. F.; Sun, X. D.; Feng, Z. J.; Huang, Z. F. Synthesis and Application of Tetramethylammonium-Carboxymethylated-β-Cyclodextrin: A Novel Ionic Liquid in Capillary Electrophoresis Enantioseparation. J. Pharm. Biomed. Anal. 2020, 180, 113030. DOI: 10.1016/j.jpba.2019.113030.
   PubMed Web of Science ®Google Scholar
• Ma, X. F.; Du, Y. X.; Sun, X. D.; Liu, J.; Huang, Z. F. Synthesis and Application of Amino Alcohol-Derived Chiral Ionic Liquids, as Additives for Enantioseparation in Capillary Electrophoresis. J. Chromatogr. A 2019, 1601, 340–349. DOI: 10.1016/j.chroma.2019.04.040.
   PubMed Web of Science ®Google Scholar
• Zhang, Q.; Zhang, J.; Xue, S.; Rui, M.; Gao, B.; Li, A.; Bai, J.; Yin, Z.; Anochie, E. M. Enhanced Enantioselectivity of Native α-Cyclodextrins by the Synergy of Chiral Ionic Liquids in Capillary Electrophoresis. J. Sep. Sci. 2018, 41, 4525–4532. DOI: 10.1002/jssc.201800792.
   PubMed Web of Science ®Google Scholar
• Banerjee-Ghosh, K.; Ben Dor, O.; Tassinari, F.; Capua, E.; Yochelis, S.; Capua, A.; Yang, S. H.; Parkin, S. S. P.; Sarkar, S.; Kronik, L.; et al. Separation of Enantiomers by Their Enantiospecific Interaction with Achiral Magnetic Substrates. Science 2018, 360, 1331. DOI: 10.1126/science.aar4265.
   PubMed Web of Science ®Google Scholar
• Li, H.; Huang, Q.; Li, D.; Li, S.; Wu, X.; Wen, L.; Ban, C. Generation of a Molecular Imprinted Membrane by Coating Cellulose Acetate onto a ZrO2-Modified Alumina Membrane for the Chiral Separation of Mandelic Acid Enantiomers. Org. Process. Res. Dev. 2018, 22, 278–285. DOI: 10.1021/acs.oprd.7b00054.
   Web of Science ®Google Scholar