☆ 4.5 Review

Recent progress in the development of chiral stationary phases for high-performance liquid chromatography

JOURNAL OF SEPARATION SCIENCE (2022)

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Article Materials Science, Paper & Wood

Cellulose phenylcarbamate-derived hybrid bead-type chiral packing materials for efficient chiral recognition

Geng Li et al.

Summary: Researchers developed eight organic-inorganic hybrid bead-type chiral packing materials with high organic contents using a modified Stober process in basic conditions. The preparation conditions significantly affected the organic contents and morphology of the hybrid materials, with those having higher organic content showing better enantioseparation ability.

CELLULOSE (2021)

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Article Chemistry, Multidisciplinary

Racemic Monomer-Based One-Handed Helical Polymer Recognizes Enantiomers through Auto-Evolution of Its Helical Handedness Excess

Tomoyuki Ikai et al.

Summary: The racemic monomer-based optically inactive polyacetylene can fold into a one-handed helix with the assistance of a nonracemic alcohol, serving as a chiral stationary phase in chromatography to separate enantiomers effectively. The polymer shows auto-evolution of helical handedness over time and enhanced optical purity of the nonracemic alcohol adsorbed on the helical polyacetylene due to chiral filter effect, contributing to increased helix-sense-excess.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Biochemical Research Methods

Unusual Difference in Enantioselectivity of Two Chiral Stationary Phases with Grafted Antibiotic Ristocetin A

Margarita Kopchenova et al.

Summary: The enantioselectivity towards hydrophilic and hydrophobic dipeptides was significantly different between the Chirobiotic R and Nautilus-R chiral stationary phases, which was explained by distinct configurations of the binding sites of the selectors and the varying number of ionizable amino groups in the grafted selectors. The retention and separation factors of enantiomers were measured using buffered and unbuffered methanol-water mixtures with different concentrations of methanol as mobile phases.

CHROMATOGRAPHIA (2021)

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Article Biochemical Research Methods

Homochiral Metal-Organic Framework [Co(L)(bpe)2(H2O)2]•H2O Used for Separation of Racemates in High-Performance Liquid Chromatography

Yunyan Yu et al.

Summary: A homochiral metal-organic framework was prepared and used as a chiral stationary phase for high-performance liquid chromatography, successfully separating nine racemates and demonstrating its potential application in HPLC.

JOURNAL OF CHROMATOGRAPHIC SCIENCE (2021)

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Article Biochemical Research Methods

A chiral metal-organic cage used as the stationary phase for gas chromatography separations

Bo Tang et al.

Summary: Chiral metal-organic cages (MOCs) have been investigated as a novel stationary phase for gas chromatography (GC) due to their unique molecular recognition ability. The chiral MOC-PA exhibited high-resolution performance for a wide range of analytes, especially for amino acid derivatives, showing excellent separation repeatability and reproducibility. The experimental results suggest that MOC-PA has great potential as a GC stationary phase.

JOURNAL OF CHROMATOGRAPHY A (2021)

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Article Biochemical Research Methods

Enantioseparation performance of superficially porous particle vancomycin-based chiral stationary phases in supercritical fluid chromatography and high performance liquid chromatography; applicability for psychoactive substances

Denisa Folprechtova et al.

Summary: Novel psychoactive substances (NPS) are synthetic compounds designed to mimic the effects of recreational drugs while avoiding current drug control laws. Chiral NPS present challenges due to limited information on the pharmacological and toxicological properties of their enantiomers. The use of vancomycin-based chiral stationary phases shows high enantioselective potential in fast separation methods for various classes of NPS in both supercritical fluid chromatography and liquid chromatography.

JOURNAL OF CHROMATOGRAPHY A (2021)

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Article Chemistry, Analytical

Enantiomer separation on novel cellulose derivatives bearing regioselective phenylcarbamate groups

Shouwan Tang et al.

Summary: Four novel regioselectively carbamoylated cellulose derivatives were synthesized and utilized as chiral stationary phases in high-performance liquid chromatography. The chiral recognition abilities of these derivatives were significantly affected by the nature and arrangement of the groups at different positions, leading to improved resolution of racemates. Investigating the influence of mobile phase on chiral recognition revealed that better resolutions were generally obtained with decreased amount of 2-propanol and poorer enantioseparations were often achieved when ethanol was used instead of 2-propanol as the mobile phase modifier.

JOURNAL OF SEPARATION SCIENCE (2021)

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Article Chemistry, Analytical

Hydroxypropyl-β-cyclodextrin encapsulated stationary phase based on silica monolith particles for enantioseparation in liquid chromatography

Yao Lu et al.

Summary: A new method for developing a chiral stationary phase for enantioseparation in liquid chromatography was introduced by incorporating hydroxypropyl-beta-cyclodextrin-encapsulated stationary phase on silica monolith particles through physical embedding. The experimental results show promising potential in separating chiral enantiomers using sol-gel ground silica particles modified with beta-cyclodextrin.

JOURNAL OF SEPARATION SCIENCE (2021)

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Article Chemistry, Multidisciplinary

Highly Stable Zr(IV)-Based Metal-Organic Frameworks for Chiral Separation in Reversed-Phase Liquid Chromatography

Hong Jiang et al.

Summary: This study demonstrates that highly stable Zr-based MOFs can be efficient CSPs for RP-HPLC. By designing and synthesizing three chiral porous Zr(IV)-MOFs with chiral crown ether moieties aligned within framework channels, they show excellent tolerance to water, acid, and base. Under acidic eluent conditions, Zr-MOF-packed HPLC columns provide high resolution, selectivity, and durability for the separation of various racemates.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Analytical

Development and validation of a fast HPLC method for methyldopa enantiomers using superficially porous particle based macrocyclic glycopeptide stationary phase

Mariana da Silva Goncalves et al.

Summary: The study evaluated different chiral stationary phases and superficially porous particles for the efficient separation of methyldopa enantiomers in reversed-phase and polar ionic elution modes. Suitable selectivity and fast analysis were achieved, with total separation obtained using the teicoplanin and teicoplanin aglycone stationary phases.

MICROCHEMICAL JOURNAL (2021)

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Article Chemistry, Analytical

2D metal-organic framework nanosheets-assembled core-shell composite material as stationary phase for hydrophilic interaction liquid chromatography

Tiantian Si et al.

Summary: The core-shell composites were successfully prepared by modifying silica spheres with two-dimensional MOF-FDM-23 nanosheets, showing excellent separation performance and high reproducibility in preparation.

TALANTA (2021)

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Review Chemistry, Multidisciplinary

Metal-organic cages for molecular separations

Dawei Zhang et al.

Summary: Metal-organic cages, formed via coordination-driven self-assembly, show great promise as separation agents by selectively binding and distinguishing substances in solution through precise control of their structure. The use of cages as absorbents or incorporation into polymer membranes can enhance the efficiency and selectivity of separation processes. Challenges and potential future developments in using metal-organic cages for separations are also discussed.

NATURE REVIEWS CHEMISTRY (2021)

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Article Chemistry, Analytical

Chiral metal-organic framework [Co2(D-cam)2(TMDPy)]@Sio2 core-shell microspheres for HPLC separation

Baoyan Yuan et al.

Summary: Chiral metal-organic frameworks (MOFs) are a promising candidate as new chiral stationary phases (CSPs) for usage in HPLC due to their uniform and adjustable cavities, abundant chiral active sites and excellent chemical stability. In this study, monodisperse homochiral MOF [Co-2(D-cam)(2)(TMDP3)]@SiO2 core-shell composites were prepared using an in-situ growth method, showing improved column efficiency and chiral resolution ability compared to conventional MOF columns. This approach provides a promising platform for the practical applications of chiral MOFs in chiral separation.

MICROCHEMICAL JOURNAL (2021)

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Article Chemistry, Analytical

Facile fabrication of silica@covalent organic polymers core-shell composites as the mixed-mode stationary phase for hydrophilic interaction/reversed-phase/ion-exchange chromatography

Jun Chen et al.

Summary: The study presents a novel mixed-mode stationary phase for HPLC based on silica@COPs core-shell composites, which exhibit flexible selectivity and superior separation performance for various types of compounds. The developed phase shows a combination of hydrophilic interaction, reversed-phase, and ion-exchange retention mechanisms, providing enhanced resolution and efficient separation of analytes.

TALANTA (2021)

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Article Biochemical Research Methods

Enantioseparation on a new synthetic β-cyclodextrin chemically bonded chiral stationary phase and molecular docking study

Meng Li et al.

Summary: A novel beta-cyclodextrin derivative chiral stationary phase (EDACD) was synthesized and evaluated for enantioselective performance with antiinflammatory drugs and flavonoids. Factors affecting enantioseparation were investigated, showing promising results with adjustments in mobile phase composition and buffers. Molecular docking study indicated that hydrogen bonding and inclusion complexation played a crucial role in chiral recognition, suggesting a wider application potential for EDACD in chiral compound analysis.

ANALYTICAL AND BIOANALYTICAL CHEMISTRY (2021)

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Article Biochemistry & Molecular Biology

Peptoids as a Chiral Stationary Phase for Liquid Chromatography: Insights from Molecular Dynamics Simulations

Sebastien Hoyas et al.

Summary: Peptoids have a high potential for diverse applications, including serving as a chiral stationary phase in chromatography, and their ability to form specific interactions with enantiomers is crucial for chiral recognition.

BIOMACROMOLECULES (2021)

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Article Chemistry, Applied

Preparation of 6-amino-6-deoxy cellulose and its derivatives used as chiral separation materials

Hong Gao et al.

Summary: This study successfully synthesized 6-amino-6-deoxy cellulose using optimized methods, which was further used to prepare cellulose derivatives with chiral selectivity. These derivatives were utilized as chiral stationary phases (CSPs) and exhibited enantioseparation power towards some chiral compounds.

CARBOHYDRATE POLYMERS (2021)

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Article Biochemical Research Methods

The interactions between chiral analytes and chitosan-based chiral stationary phases during enantioseparation

Wei Chen et al.

Summary: The present study aimed to investigate the interactions between chitosan-type chiral selectors and chiral analytes in enantioseparation. Through synthesizing and characterizing chitosan derivatives and evaluating their enantioseparation capability, the study highlighted the importance of substituents on the phenyl group in chiral recognition mechanism. The study also shed light on the role of hydrogen bonding formation in enantioseparation and the impact of different mobile phases on the process.

JOURNAL OF CHROMATOGRAPHY A (2021)

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Article Biochemical Research Methods

Preparation and characterization of poly(3-mercaptopropyl)methylsiloxane functionalized silica particles and their further modification for silver ion chromatography and enantioselective high-performance liquid chromatography

Marc Wolter et al.

Summary: This work presents the preparation of polythiol-functionalized silica particles using radical addition reactions, demonstrating their utility in various HPLC applications. Factors such as quantity of PMPMS, radical starter, and reaction time were investigated to achieve a sulfhydryl group-rich PMPMS layer on the silica surface. The thiol-functionalized silica particles were further modified for silver ion chromatography and chiral separation chromatography, showing promising separation abilities for different analytes.

JOURNAL OF CHROMATOGRAPHY A (2021)

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Article Biochemical Research Methods

Striped covalent organic frameworks modified stationary phase for mixed mode chromatography

Yunchao Zheng et al.

Summary: Covalent organic frameworks (COFs) have great potential in chromatographic separations due to their unique structure and performance. The modified SiO2@COF stationary phase demonstrated mixed-mode separation abilities with various interaction modes, showing promise for complex sample analysis.

JOURNAL OF CHROMATOGRAPHY A (2021)

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Review Chemistry, Analytical

Preparation and applications of cellulose-functionalized chiral stationary phases: A review

Xiaoping Wang et al.

Summary: Separation and identification of chiral enantiomers are increasingly important in various fields like pharmaceutical production, chemical intermediates preparation, and biochemistry. Cellulose and its derivatives, with strong chiral recognition ability, large loading capacity and ease of functionalization, have shown excellent performance in enantioseparation, indicating great potential in chiral separation. This review systematically summarizes the types of cellulose derivatives, preparation of cellulose-functionalized chiral stationary phases, and their recent applications in chiral chromatographic separation, aiming to provide a useful reference for researchers and inspire new discoveries in the field.

TALANTA (2021)

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Article Polymer Science

Influence of surfactants on the properties of cellulose derivative-based hybrid materials as chiral stationary phases

Geng Li et al.

Summary: The research investigates the enantioseparation performance of hybrid bead-type CSPs with higher organic content, revealing their stronger enantioseparation power compared to those with lower organic content and previous analogous CSPs. The hybrid CSPs also exhibit higher enantioselectivity than Chiralpak IB, a popular commercialized CSP. Furthermore, the higher loading capacity of the hybrid CSPs is beneficial for efficient enantioseparation, especially for preparative purposes.

EUROPEAN POLYMER JOURNAL (2021)

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Article Biochemical Research Methods

Enantioseparation of β2-amino acids by liquid chromatography using core-shell chiral stationary phases based on teicoplanin and teicoplanin aglycone

Daniel Tanacs et al.

Summary: This study performed enantioseparation of nineteen $(2)-amino acids using chiral stationary phases based on native teicoplanin and teicoplanin aglycone. The separation was carried out in different modes and mobile phases, with the structure of selectands and selectors found to significantly influence the separation performance. Analysis of van Deemter plots and determination of thermodynamic parameters were performed to further investigate the details of the separation performance.

JOURNAL OF CHROMATOGRAPHY A (2021)

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Article Chemistry, Analytical

Enantioseparation and modelling study of six proton pump inhibitors on a novel 3, 5-dichloro-phenylcarbamated fl-cyclodextrin chemically bonded chiral stationary phase by high performance liquid chromatography

Meng Li et al.

Summary: A chiral stationary phase MDCPC, prepared by linking a fully substituted fl-cyclodextrin derivative to a silica support, showed excellent enantioselectivity and stability in high performance liquid chromatography. The study demonstrated successful chiral separation of target compounds through systematic evaluation and molecular docking analysis, suggesting promising prospects for further analysis of chiral drugs.

MICROCHEMICAL JOURNAL (2021)

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Article Chemistry, Analytical

Click preparation of multiple-thioether bridged cyclodextrin chiral materials for efficient enantioseparation in high-performance liquid chromatography†

Ming Chen et al.

Summary: This study demonstrates a highly efficient covalent immobilization procedure to prepare stable and reliable cyclodextrin chiral stationary phases with novel multiple-thioether bridging. Through controlling the surface concentration of cyclodextrin, the stationary phases showed superior enantioseparation ability in reversed-phase HPLC mode, successfully resolving over 60 chiral enantiomers.

ANALYST (2021)

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Article Chemistry, Multidisciplinary

Synthesis and characterization of cellulose derivative-based hybrid beads as chiral stationary phases for efficient chromatographic enantioseparation†

Geng Li et al.

Summary: Four hybrid bead-type CSPs with organic contents higher than 20% were developed using a modified Stober process in basic conditions, showing better enantioseparation properties than previous analogues. These hybrid CSPs exhibited higher enantioselectivity than the commercial Chiralpak IB in some cases.

NEW JOURNAL OF CHEMISTRY (2021)

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Article Polymer Science

Enantioseparation by high-performance liquid chromatography on proline-derived helical polyacetylenes

Ge Shi et al.

Summary: The research systematically explored the correlations among the nature, size, and position of the substituent on the phenyl ring with the polymer conformation and enantioseparation performance using NMR, Raman and UV-absorption spectroscopy, polarimetry, circular dichroism, HPLC, and computational simulation. It was found that the strength of the hydrogen bond and pi-pi interactions between enantiomers and CSPs played a remarkable role in enantioseparation.

POLYMER CHEMISTRY (2021)

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Review Chemistry, Analytical

Chiral porous organic frameworks and their application in enantioseparation

Ying Zhang et al.

Summary: Porous organic frameworks (POFs) are porous materials with excellent physical and chemical properties, which have attracted broad interest. Metal organic frameworks (MOFs) and covalent organic frameworks (COFs) have been widely applied in fields such as luminous materials and catalytic research, while chiral porous materials play important roles in chiral separation.

ANALYTICAL METHODS (2021)

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Article Chemistry, Analytical

Enantioselective resolutions by high-performance liquid choromatography using chiral inorganic mesoporous silica

Wan-Qi Xiong et al.

Summary: Four chiral hexagonal ordered mesoporous silica materials were synthesized using self-assembly and templated by surface active agents derived from amino acids. These materials were utilized to prepare chromatographic columns for separating chiral compounds and positional isomers with good separation effects and potential practical value.

SEPARATION SCIENCE PLUS (2021)

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Article Chemistry, Applied

New composite stationary phase for chiral high-performance liquid chromatography

D. S. Prosuntsova et al.

Summary: A new composite chiral stationary phase for high-performance liquid chromatography was prepared using gold nanoparticles coated polystyrene-divinylbenzene microspherical particles, with l-lysine conjugate with lipoic acid utilized for enhancing chiral selectivity. The immobilization of the chiral selector was achieved by the reaction of sulfur-containing groups from lipoic acid residue with the gold surface of nanoparticles, enabling successful enantiomers separation for flurbiprofen and ketoprofen.

JOURNAL OF POROUS MATERIALS (2021)

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Article Polymer Science

Influence of phenyl group number on enantioseparation performance of chitosan-based materials

Wei Chen et al.

Summary: The research found that increasing the number of phenyl groups in chitosan derivatives can improve enantioseparation capability, but one phenyl group is not sufficient for separation; two or three phenyl groups are needed.

JOURNAL OF APPLIED POLYMER SCIENCE (2021)

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Article Biochemical Research Methods

Separation of enantiomers of chiral sulfoxides in high-performance liquid chromatography with cellulose-based chiral selectors using acetonitrile and acetonitrile-water mixtures as mobile phases

Zoia Shedania et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Article Chemistry, Medicinal

Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)-bonded chiral stationary phase for HPLC

Yazhou Shuang et al.

CHIRALITY (2020)

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Article Chemistry, Medicinal

New chiral stationary phases for liquid chromatography based on small molecules: Development, enantioresolution evaluation and chiral recognition mechanisms

Ye' Zaw Phyo et al.

CHIRALITY (2020)

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Article Biochemical Research Methods

An azine-linked covalent organic framework as stationary phase for separation of environmental endocrine disruptors by open-tubular capillary electrochromatography

Lingyi Zhao et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Article Biochemical Research Methods

Preparation of a stilbene diamido-bridged bis(β-cyclodextrin)-bonded chiral stationary phase for enantioseparations of drugs and pesticides by high performance liquid chromatography

Yazhou Shuang et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Review Chemistry, Analytical

Recent advances of application of porous molecular cages for enantioselective recognition and separation

Jun-Hui Zhang et al.

JOURNAL OF SEPARATION SCIENCE (2020)

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Article Chemistry, Medicinal

Preparation and evaluation of biselector bonded-type multifunctional chiral stationary phase based on dialdehyde cellulose and 6-monodeoxy-6-monoamino-β-cyclodextrine derivatives

Jie Gao et al.

CHIRALITY (2020)

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Article Chemistry, Medicinal

Synthesis of poly(phenylacetylene)s containing chiral phenylethyl carbamate residues as coated-type CSPs with high solvent tolerability

Yanli Zhou et al.

CHIRALITY (2020)

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Article Biochemical Research Methods

Preparation and evaluation of an ethylenediamine dicarboxyethyl diamido-bridged bis(β-cyclodextrin)-bonded chiral stationary phase for high performance liquid chromatography

Yazhou Shuang et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Article Biochemical Research Methods

A new strategy for the preparation of mixed-mode chromatographic stationary phases based on modified dialdehyde cellulose

Jie Gao et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Article Biochemical Research Methods

Thermoresponsive chiral stationary phase functionalized with the copolymer of β-cyclodextrin and N-isopropylacrylamide for high performance liquid chromatography

Xiujun Ren et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Review Chemistry, Analytical

Recent trends in preparation, investigation and application of polysaccharide-based chiral stationary phases for separation of enantiomers in high-performance liquid chromatography

Bezhan Chankvetadze

TRAC-TRENDS IN ANALYTICAL CHEMISTRY (2020)

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Review Chemistry, Analytical

Enantioseparation using helical polyacetylene derivatives

Chunhong Zhang et al.

TRAC-TRENDS IN ANALYTICAL CHEMISTRY (2020)

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Review Chemistry, Analytical

Chiral analysis in food science

Gerardo Alvarez-Rivera et al.

TRAC-TRENDS IN ANALYTICAL CHEMISTRY (2020)

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Article Nanoscience & Nanotechnology

Chiral Metal-Organic Framework D-His-ZIF-8@SiO2 Core-Shell Microspheres Used for HPLC Enantioseparations

Yunyan Yu et al.

ACS APPLIED MATERIALS & INTERFACES (2020)

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Article Chemistry, Analytical

Enantiomeric Separation of Chiral Triazole Pesticides by a mono-6-(4-Nitrophenyl)-ureido-β-cyclodextrin-Bonded Stationary Phase Using High-Performance Liquid Chromatography

Yazhou Shuang et al.

ANALYTICAL LETTERS (2020)

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Article Chemistry, Medicinal

Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety

Lunan Zhu et al.

CHIRALITY (2020)

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Article Engineering, Chemical

De novo synthesis of microspheical cellulose 3,5-dichlorophenylcarbamates: An organic-inorganic hybrid chiral stationary phase for enantiospearation

Xiaoxiao Yu et al.

SEPARATION AND PURIFICATION TECHNOLOGY (2020)

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Article Chemistry, Analytical

Imidazolium ionic liquid-enhanced poly(quinine)-modified silica as a new multi-mode chromatographic stationary phase for separation of achiral and chiral compounds

Hang Zhou et al.

TALANTA (2020)

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Article Chemistry, Analytical

A novel C2 symmetric chiral stationary phase with N-[(4-Methylphenyl)sulfonyl]-l-leucine as chiral side chains

Junchen Zhu et al.

JOURNAL OF SEPARATION SCIENCE (2020)

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Article Biochemical Research Methods

Preparation and Application of Partially Substituted Phenylcarbamate-(3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-Appended Silica Particles as Chiral Stationary Phase for Multi-mode HPLC

Jingxuan Yi et al.

CHROMATOGRAPHIA (2020)

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Article Chemistry, Applied

Influence of the substituents on phenyl groups on enantioseparation property of amylose phenylcarbamates

Wanying Bi et al.

CARBOHYDRATE POLYMERS (2020)

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Article Biochemical Research Methods

Polysaccharide-Based Chiral Stationary Phases on Gold Nanoparticles Modified Silica Beads for Liquid-Phase Separation of Enantiomers

Yuanyuan Li et al.

JOURNAL OF CHROMATOGRAPHIC SCIENCE (2020)

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Article Biochemical Research Methods

Enantioseparation using chitosan 2-isopropylthiourea-3,6-dicarbamate derivatives as chiral stationary phases for high-performance liquid chromatography

Lili Zhang et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Article Biochemical Research Methods

Chiral stationary phase based on cellulose derivative coated polymer microspheres and its separation performance

Lin Li et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Article Biochemical Research Methods

β-Cyclodextrin porous polymers with three-dimensional chiral channels for separation of polar racemates

Yanlong Chen et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Article Biochemical Research Methods

Comparison in enantioseparation performance of chiral stationary phases prepared from chitosans of different sources and molecular weights

Gui-Hua Zhang et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Article Biochemical Research Methods

Fragment-based Design of Zwitterionic, Strong Cation- and Weak Anion-Exchange Type Mixed-mode Liquid Chromatography Ligands and their Chromatographic Exploration

Martina Ferri et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Article Biochemical Research Methods

Enantioselective ultra-high performance liquid chromatography-tandem mass spectrometry method based on sub-2μm particle polysaccharide column for chiral separation of oxylipins and its application for the analysis of autoxidized fatty acids and platelet releasates

Malgorzata Cebo et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Article Biochemical Research Methods

Synthesis of a poly(diphenylacetylene) bearing optically active anilide pendants and its application to a chiral stationary phase for high-performance liquid chromatography

Mai Nozaki et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Article Biochemical Research Methods

Thiol-ene photo-click immobilization of a chiral chromatographic ligand on silica particles

Christian Geibel et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Article Chemistry, Multidisciplinary

Synthesis and Application of New Calix[4]Arenes-Containing (R)-Phenylglycinol Chiral Stationary Phases for Enantioseparation

Kyu Sung Heo et al.

BULLETIN OF THE KOREAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Analytical

Preparation of a teicoplanin-bonded chiral stationary phase for simultaneous determination of clenbuterol and salbutamol enantiomers in meat by LC-MS/MS

Liang Li et al.

MICROCHEMICAL JOURNAL (2020)

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Article Chemistry, Analytical

Preparation and performance of a poly(ethyleneimine) embedded N-acetyl-L-phenylalanine mixed-mode stationary phase for HPLC

Meijun Wan et al.

MICROCHEMICAL JOURNAL (2020)

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Article Chemistry, Analytical

Controlled fabrication of core-shell silica@chiral metal-organic framework for significant improvement chromatographic separation of enantiomers

Cuijie Wang et al.

TALANTA (2020)

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Article Chemistry, Multidisciplinary

Enantioseparation on AminoAlcohol-DerivedStationary Phases by Supercritical Fluid Chromatography and High-Performance Liquid Chromatograpy

Gyuri Kim et al.

BULLETIN OF THE KOREAN CHEMICAL SOCIETY (2020)

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Article Biochemical Research Methods

Ionic liquid functionalized β-cyclodextrin and C18 mixed-mode stationary phase with achiral and chiral separation functions

Jingqiu Zhou et al.

JOURNAL OF CHROMATOGRAPHY A (2020)

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Review Chemistry, Multidisciplinary

Chiral covalent organic frameworks: design, synthesis and property

Xing Han et al.

CHEMICAL SOCIETY REVIEWS (2020)

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Article Polymer Science

Synthesis and enantioseparation of proline-derived helical polyacetylenes as chiral stationary phases for HPLC

Ge Shi et al.

POLYMER CHEMISTRY (2020)

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Review Chemistry, Multidisciplinary

Covalent organic frameworks for separation applications

Zhifang Wang et al.

CHEMICAL SOCIETY REVIEWS (2020)

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Review Chemistry, Multidisciplinary

Bulk COFs and COF nanosheets for electrochemical energy storage and conversion

Jie Li et al.

CHEMICAL SOCIETY REVIEWS (2020)

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Review Chemistry, Analytical

Recent development trends for chiral stationary phases based on chitosan derivatives, cyclofructan derivatives and chiral porous materials in high performance liquid chromatography

Sheng-Ming Xie et al.

JOURNAL OF SEPARATION SCIENCE (2019)

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Article Biochemical Research Methods

Click regulation of cyclodextrin primary face for the preparation of novel chiral stationary phases

Xuan Jin et al.

ELECTROPHORESIS (2019)

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Article Biochemical Research Methods

Wide pH range enantioseparation of cyclodextrin silica-based hybrid spheres for high performance liquid chromatography

Litao Wang et al.

JOURNAL OF CHROMATOGRAPHY A (2019)

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Article Polymer Science

Effective Separation of Enantiomers Based on Novel Chiral Hierarchical Porous Metal-Organic Gels

Yu Ma et al.

MACROMOLECULAR RAPID COMMUNICATIONS (2019)

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Article Engineering, Chemical

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Graphene quantum dots functionalized β-cyclodextrin and cellulose chiral stationary phases with enhanced enantioseparation performance

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Three-State Switchable Chiral Stationary Phase Based on Helicity Control of an Optically Active Poly(phenylacetylene) Derivative by Using Metal Cations in the Solid State

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Preparation and chiroptical properties of cellulose chlorophenylcarbamate-silica hybrids having a chiral nematic mesomorphic structure

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Preparation of a new benzylureido-β-cyclodextrin-based column and its application for the determination of phenylmercapturic acid and benzylmercapturic acid enantiomers in human urine by LC/MS/MS

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Structure screening and performance restoration of chiral separation materials based on chitosan derivatives

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Preparation and chromatographic performance of a multifunctional immobilized chiral stationary phase based on dialdehyde microcrystalline cellulose derivatives

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Evaluation of superficially porous particle based zwitterionic chiral ion exchangers against fully porous particle benchmarks for enantioselective ultra-high performance liquid chromatography

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Regioselectively substituted cellulose mixed esters synthesized by two-steps route to understand chiral recognition mechanism and fabricate high-performance chiral stationary phases

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Dependence of enantioseparation performance on structure of chiral selectors derived from N-cycloalkylcarbonyl chitosan

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The preparation of a new 3,5-dichlorophenylcarbamated cellulose-bonded stationary phase and its application for the enantioseparation and determination of chiral fungicides by LC-MS/MS

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A fully derivatized 4-chlorophenylcarbamate-β-cyclodextrin bonded chiral stationary phase for enhanced enantioseparation in HPLC

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Performances comparison of enantiomeric separation materials prepared from shrimp and crab shells

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A novel homochiral metal-organic framework with an expanded open cage based on (R)-3,3′-bis(6-carboxy-2-naphthyl)-2,2′-dihydroxy-1,1′-binaphthyl: synthesis, X-ray structure and efficient HPLC enantiomer separation

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Performance evaluation of enantioseparation materials based on chitosan isobutylurea derivatives

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Preparation and evaluation of partially-substituted 3-chloro-4-methylphenylcarbamate-β-cyclodextrin bonded silica particles as chiral stationary phase for multi-mode HPLC

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Helicity induction and memory effect in poly(biphenylylacetylene)s bearing various functional groups and their use as switchable chiral stationary phases for HPLC

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Comparative study on the liquid chromatographic enantioseparation of cyclic beta-amino acids and the related cyclic beta-aminohydroxamic acids on Cinchona alkaloid-based zwitterionic chiral stationary phases

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Exploring the enantiorecognition mechanism of Cinchona alkaloid-based zwitterionic chiral stationary phases and the basic trans-paroxetine enantiomers

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Separations at the Speed of Sensors

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Homochiral Metal-Organic Cage for Gas Chromatographic Separations

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Controllable synthesis of cellulose benzoates for understanding of chiral recognition mechanism and fabrication of highly efficient chiral stationary phases

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Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

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Separation of beta-Blocker Enantiomers on Silica Modified with Gold Nanoparticles with Immobilized Macrocyclic Antibiotic Vancomicin

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Performance comparison of chiral separation materials derived from N-cyclohexylcarbonyl and N-hexanoyl chitosans

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Comparison of small size fully porous particles and superficially porous particles of chiral anion-exchange type stationary phases in ultra-high performance liquid chromatography: effect of particle and pore size on chromatographic efficiency and kinetic performance

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Effective methodologies for enantiomeric separations of 150 pharmacology and toxicology related 1°, 2°, and 3° amines with core-shell chiral stationary phases

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Effect of different immobilization strategies on chiral recognition properties of Cinchona-based anion exchangers

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Thiol-ene click derived structurally well-defined per(3,5-dimethyl)phenylcarbamoylated cationic cyclodextrin separation material for achiral and chiral chromatography

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Chiral 3D Covalent Organic Frameworks for High Performance Liquid Chromatographic Enantioseparation

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A cationic cyclodextrin clicked bilayer chiral stationary phase for versatile chiral separation in HPLC

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Polarity tuned perphenylcarbamoylated cyclodextrin separation materials for achiral and chiral differentiation

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A high-performance chiral selector derived from chitosan (p-methylbenzylurea) for efficient enantiomer separation

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Light-assisted preparation of vancomycin chiral stationary phase based on diazotized silica and its enantioseparation evaluation by high-performance liquid chromatography

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Preparation and chromatographic evaluation of a chiral stationary phase based on carboxymethyl-β-cyclodextrin for high-performance liquid chromatography

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Synthesis of cellulose carbamates bearing regioselective substituents at 2,3-and 6-positions for efficient chromatographic enantioseparation

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Stationary phase based on cellulose dodecanoate physically immobilized on silica particles for high-performance liquid chromatography

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On our way to sub-second separations of enantiomers in high-performance liquid chromatography

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Application of cellulose 3,5-dichlorophenylcarbamate covalently immobilized on superficially porous silica for the separation of enantiomers in high-performance liquid chromatography

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Covalent Organic Frameworks with Chirality Enriched by Biomolecules for Efficient Chiral Separation

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Homochiral metal-organic framework immobilized on silica gel by the interfacial polymerization for HPLC enantioseparations

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Synthesis of a Novel Chiral Stationary Phase by (R)-1,1′-Binaphthol and the Study on Mechanism of Chiral Recognition

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Preparation of Cyclodextrin Type Stationary Phase Based on Graphene Oxide and Its Application in Enantioseparation and Hydrophilic Interaction Chromatography

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Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations

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Preparation of polysaccharide-based chiral stationary phases on SiO2@Ag core-shell particles by means of coating and intermolecular polycondensation and comparative liquid chromatography enantioseparations

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A new single-urea-bound 3,5-dimethylphenylcarbamoylated beta-cyclodextrin chiral stationary phase and its enhanced separation performance in normal-phase liquid chromatography

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Construction of a hydrazone-linked chiral covalent organic framework-silica composite as the stationary phase for high performance liquid chromatography

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Effect of pore-size optimization on the performance of polysaccharide-based superficially porous chiral stationary phases for the separation of enantiomers in high-performance liquid chromatography

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Static Memory of Enantiomeric Helices Induced in a Poly(biphenylylacetylene) by a Single Enantiomer Assisted by Temperature- and Solvent-Driven Helix Inversion

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In situ synthesis of the imine-based covalent organic framework LZU1 on the inner walls of capillaries for electrochromatographic separation of nonsteroidal drugs and amino acids

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Efficient Separation of Enantiomers Using Stereoregular Chiral Polymers

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Engineering Thiol-Ene Click Chemistry for the Fabrication of Novel Structurally Well-Defined Multifunctional Cyclodextrin Separation Materials for Enhanced Enantioseparation

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Chiral Recognition Ability of an Optically Active Poly(diphenylacetylene) as a Chiral Stationary Phase for HPLC

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Further proof to the utility of polysaccharide-based chiral selectors in combination with superficially porous silica particles as effective chiral stationary phases for separation of enantiomers in high-performance liquid chromatography

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Synthesis of Optically Active Poly(diphenylacetylene)s Using Polymer Reactions and an Evaluation of Their Chiral Recognition Abilities as Chiral Stationary Phases for HPLC

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Bottom-up synthesis of chiral covalent organic frameworks and their bound capillaries for chiral separation

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Homochiral Porous Organic Cage with High Selectivity for the Separation of Racemates in Gas Chromatography

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Gone in Seconds: Praxis, Performance, and Peculiarities of Ultrafast Chiral Liquid Chromatography with Superficially Porous Particles

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A novel inorganic mesoporous material with a nematic structure derived from nanocrystalline cellulose as the stationary phase for high-performance liquid chromatography

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Two-Dimensional Covalent Organic Frameworks for Carbon Dioxide Capture through Channel-Wall Functionalization

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3D Porous Crystalline Polyimide Covalent Organic Frameworks for Drug Delivery

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Novel Inorganic Mesoporous Material with Chiral Nematic Structure Derived from Nanocrystalline Cellulose for High-Resolution Gas Chromatographic Separations

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Synthesis of chitosan 3,6-diphenylcarbamate-2-urea derivatives and their applications as chiral stationary phases for high-performance liquid chromatography

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Thiol-ene click chemistry derived cationic cyclodextrin chiral stationary phase and its enhanced separation performance in liquid chromatography

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Switchable enantioseparation based on macromolecular memory of a helical polyacetylene in the solid state

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Fabrication of ZIF-8@SiO2 Core-Shell Microspheres as the Stationary Phase for High-Performance Liquid Chromatography

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Influence of stereoregularity and linkage groups on chiral recognition of poly(phenylacetylene) derivatives bearing L-leucine ethyl ester pendants as chiral stationary phases for HPLC

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ACCOUNTS OF CHEMICAL RESEARCH (2012)

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Chiral Separations: A Review of Current Topics and Trends

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Comparative high-performance liquid chromatography enantioseparations on polysaccharide based chiral stationary phases prepared by coating totally porous and core-shell silica particles

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The Significance of Chirality in Drug Design and Development

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Improved preparation of chiral stationary phases via immobilization of polysaccharide derivative-based selectors using diisocyanates

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Chiral Metal-Organic Frameworks for High-Resolution Gas Chromatographic Separations

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Construction of Covalent Organic Framework for Catalysis: Pd/COF-LZU1 in Suzuki-Miyaura Coupling Reaction

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Immobilization and Chiral Recognition of 3,5-Dimethylphenylcarbamates of Cellulose and Amylose Bearing 4-(Trimethoxysilyl)phenylcarbamate Groups

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Transition from enantioselective high performance to ultra-high performance liquid chromatography: A case study of a brush-type chiral stationary phase based on sub-5-micron to sub-2-micron silica particles

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Free-standing mesoporous silica films with tunable chiral nematic structures

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Development of New HPLC Chiral Stationary Phases Based on Native and Derivatized Cyclofructans

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NATURE MATERIALS (2009)

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Enantioselective chromatographic resolution and one-pot synthesis of enantiomerically pure sulfoxides over a homochiral Zn-organic framework

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Chemical immobilization of azido cellulose phenylcarbamate onto silica gel via Staudinger reaction and its application as a chiral stationary phase for HPLC

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Highly efficient immobilization of Cinchona alkaloid derivatives to silica gel via click chemistry

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Synthesis, chiroptical properties, and chiral recognition ability of optically active polymethacrylamides having various tacticities

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Chiral ionic liquids as stationary phases in gas chromatography

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Synthesis and characterization of chiral mesoporous silica

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Review Biochemical Research Methods

Covalently bonded polysaccharide derivatives as chiral stationary phases in high-performance liquid chromatography

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