Preparation of chiral stationary phase based on a [3+3] chiral polyimine macrocycle by thiol-ene click chemistry for enantioseparation in normal-phase and reversed-phase high performance liquid chromatography

Zhang, Youping; Xiong, Ling-Xiao; Wang, Ying; Li, Kuan; Wang, Bang-Jin; Xie, Sheng‐Ming; Zhang, Junhui; Yuan, Li‐Ming

doi:10.1016/j.chroma.2022.463253

Cited by 14 publications

(3 citation statements)

References 56 publications

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“…POCs are soluble porous materials linked with cage-like monomers . The formed inherent cavities are of benefit to the host–guest interaction and chiral recognition, but the exploration of POCs as HPLC CSPs is rare.…”

Section: Chromatographymentioning

confidence: 99%

Recent Advances in Separation and Analysis of Chiral Compounds

Yan

2023

Anal. Chem.

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Section: Chromatographymentioning

confidence: 99%

Recent Advances in Separation and Analysis of Chiral Compounds

Yan

2023

Anal. Chem.

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“…Only recently, Chaix, He, , Dey, − Liu, Ding, and co-workers have proven the ability of macrocyclic chiral polyimines to selectively capture gases or to recognize and separate small organic molecules. − However, only little is known about the similar properties of the reduced counterparts of macrocyclic polyimines. This is apparently due to much higher structural dynamics of polyamines resulting in the adaptation of different conformations by the given macrocycle .…”

Section: Introductionmentioning

confidence: 99%

Unravelling Structural Dynamics, Supramolecular Behavior, and Chiroptical Properties of Enantiomerically Pure Macrocyclic Tertiary Ureas and Thioureas

2022

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The introduction of urea or thiourea functionality to the macrocycle skeleton represents an alternative way to control conformational dynamics of chiral, polyamines of a figure-shaped periodical structure. Formally highly symmetrical, these macrocycles may adapt diverse conformations, depending on the nature of an amide linker and on a substitution pattern within the aromatic units. The type of heteroatom X in the N−C(�X)−N units present in each vertex of the macrocycle core constitutes the main factor determining the chiroptical properties. In contrast to the urea-containing derivatives, the electronic circular dichroism of thioureas is controlled by the chiral neighborhood closest to the chromophore. The dynamically induced exciton couplet is observed when the biphenyl chromophores are present in the macrocycle core. In the solid state, the seemingly disordered molecules may create ordered networks stabilized by intermolecular S•••halogen, H•••halogen, and S•••H interactions. The presence of two bromine substituents in each aromatic unit in thiourea-derived trianglamine gives rise to a self-sorting phenomenon in the crystal. In solution, this particular macrocycle exists as a dynamic equimolar mixture of two conformational diastereoisomers, differing in the spatial (clockwise and counter clockwise) arrangement of the C−Br bonds. In the crystal lattice, macrocycles of a given handedness assemble into homohelical layers.

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“…further investigated the chiral separation potential of chiral POCs for HPLC. The novel chiral POCs, NC4‐R, POC‐1, and CC19‐R have also been explored as CSPs in HPLC [98–100]. All three CSPs were also prepared by a similar strategy as NC1‐R CSPs of the mild thiol‐ene click reaction.…”

Section: The Four Chiral Porous Crystal Materials As Csps For Hplcmentioning

confidence: 99%

Recent progress for chiral stationary phases based on chiral porous materials in high‐performance liquid chromatography and gas chromatography separation

Wang,

Luo

et al. 2024

J of Separation Science

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Chirality is a fundamental property of nature. Separation and analysis of racemates are of great importance in the fields of medicine and the production of chiral biopharmaceutical intermediates. Chiral chromatography has the characteristics of a wide separation range, fast separation speed, and high efficiency. The development and preparation of novel chiral stationary phases with good chiral recognition and separation capacity is the core and key of chiral chromatographic separation and analysis. In this work, the representative research progress of novel chiral porous crystal materials including chiral covalent organic frameworks, chiral porous organic cages, chiral metal‐organic frameworks, and chiral metal‐organic cages used as chiral stationary phases of capillary gas chromatography and high‐performance liquid chromatography over the last 4 years is reviewed in detail. The chiral recognition and separation properties of the representative studies in this review are also introduced and discussed.

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Preparation of chiral stationary phase based on a [3+3] chiral polyimine macrocycle by thiol-ene click chemistry for enantioseparation in normal-phase and reversed-phase high performance liquid chromatography

Cited by 14 publications

References 56 publications

Recent Advances in Separation and Analysis of Chiral Compounds

Recent Advances in Separation and Analysis of Chiral Compounds

Unravelling Structural Dynamics, Supramolecular Behavior, and Chiroptical Properties of Enantiomerically Pure Macrocyclic Tertiary Ureas and Thioureas

Recent progress for chiral stationary phases based on chiral porous materials in high‐performance liquid chromatography and gas chromatography separation

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