Chiral pillar[5]arene-functionalized silica microspheres: synthesis, characterization and enantiomer separation

Shi, Chengxiang; Li, Hui; Shi, Xiaojie; Zhao, Liang; Qiu, Hongdeng

doi:10.1039/d1cc06978k

Cited by 18 publications

(5 citation statements)

References 38 publications

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“…Constructing host-guest inclusions between macrocyclic host molecules and free guest molecules provides unique and excellent physicochemical properties. 33,34 The common macrocyclic molecules are cyclodextrins (CD), crown ethers (CE), cupric aromatics, and cucurbituril hydrate. The introduction of macrocyclic copolymer monomers with hydrogen bonding acceptor sites into deep eutectic systems through different strategies to obtain deep eutectic polymers is desirable due to the hydrogen bond interactions between SP and DES molecules.…”

Section: Introductionmentioning

confidence: 99%

Green materials with promising applications: cyclodextrin-based deep eutectic supramolecular polymers

Zhang

Yao

et al. 2023

Green Chem.

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Section: Introductionmentioning

confidence: 99%

Green materials with promising applications: cyclodextrin-based deep eutectic supramolecular polymers

Zhang

Yao

et al. 2023

Green Chem.

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“…Qiu's group has reviewed the application of chiral pillararene in analytical chemistry and developed some macrocycle-modified stationary phases [18][19][20]. However, limited by the multi-step modification and expensive raw material, there are only a few reports of pillararene derivatives in the chromatographic stationary phase, including a direct coating on gas chromatographic columns [21][22][23][24] and chemical bonding onto carriers for LC [25][26][27] or CE [28]. However, these protocols of pillararene-based bonded silica often produce a stationary phase with less pillar [5]arene units, thus limiting the number of recognition sites.…”

Section: Introductionmentioning

confidence: 99%

One‐pot synthesis of pillar[5]quinone‐amine polymer coated silica as stationary phase for high‐performance liquid chromatography

Xie

et al. 2023

J of Separation Science

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To expand the application of pillararene in chromatographic separation, we designed and fabricated a pillar[5]quinone‐amine polymer coated silica through quinone‐amine reaction by facile one‐pot synthesis method, which was applied as a stationary phase for high‐performance liquid chromatography. Separation of hydrophobic compounds, hydrophilic compounds, halogenated aromatic compounds, and 11 aromatic positional isomers was achieved successfully in this stationary phase. Reverse‐phase separation mode and hydrophilic‐interaction separation mode were proved to exist, indicating the potential application of the mix‐mode stationary phase. Studies of chromatographic retention behavior and molecular simulation showed that multiple interactions might play an important role in the separation process, including hydrophobic interaction, hydrogen‐bonding interaction, aromatic π‐π interaction, electron donor‐acceptor interaction, and host‐guest interaction. Column repeatability and stability were tested, which showed relative standard deviations of retention time less than 0.2% for continuous 11 injections, and the durability relative standard deviations of retention time were less than 0.91% after 90 days. This novel design strategy would broaden the application of pillararene‐based covalent organic polymer in chromatography and separation science.

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“…Pillararenes are a new class of macrocyclic hosts with pillared architectures and electron-rich, hydrophobic cavities [22][23][24][25]. The pillar-shaped architectures and multifunctional cavities of pillararenes endow them with a strong ability to selectively form inclusion complexes with diverse guests, which in turn endows them with good applicability in molecular recognition and separation [26][27][28] as well as chromatographic separation [29][30][31][32]. Pillar[n]trianglimines are a new family of macrocycles with triangular, pillar-shaped geometries, which are formed by the reversible cycloimination reaction of diamines with dialdehydes [33][34][35].…”

Section: Introductionmentioning

confidence: 99%

A novel pillar[3]trianglimine macrocycle with a deep cavity used as a chiral selector to prepare a chiral stationary phase by thiol‐ene click reaction for enantioseparation in high‐performance liquid chromatography

Liang

Xiang

et al. 2023

J of Separation Science

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A chiral pillar[3]trianglimine (C60H72N6O6) with a deep cavity has been developed as a chiral selector and bonded to thiolated silica by thiol‐ene click reaction to fabricate a novel chiral stationary phase for enantioseparation in high‐performance liquid chromatography. The enantioseparation performance of the fabricated chiral stationary phase has been evaluated by separating various racemic compounds, including alcohols, esters, amines, ketones, amino acids, and epoxides, in both normal‐phase and reversed‐phase elution modes. In total, 14 and 17 racemates have been effectively separated in these two separation modes, respectively. In comparison with two widely used chiral columns (Chiralcel OD‐H and Chiralpak AD‐H), our novel chiral stationary phase offered good chiral separation complementarity, separating some of the tested racemates that could not be separated or were only partially separated on these two commercial columns. The influences of analyte mass, mobile phase composition, and column temperature on chiral separation have been investigated. Good repeatability, stability, and column‐to‐column reproducibility of the chiral stationary phase for enantioseparation have been observed. After the fabricated column had been eluted up to 400 times, the relative standard deviations (n = 5) of resolution (Rs) and retention time of the separated analytes were < 0.39% and < 0.20%, respectively. The relative standard deviations (n = 3) of Rs and retention time for column‐to‐column reproducibility were < 4.6% and < 5.2%, respectively. This study demonstrated that the new chiral stationary phase has great prospects for chiral separation in high‐performance liquid chromatography.

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Chiral pillar[5]arene-functionalized silica microspheres: synthesis, characterization and enantiomer separation

Abstract: Chiral pillar[5]arene-functionalized silica microspheres were prepared and characterized for the first time, which can be used as a new kind of chiral stationary phases for effective enantioseparation under reversed-phase and...

Cited by 18 publications

References 38 publications

Green materials with promising applications: cyclodextrin-based deep eutectic supramolecular polymers

Green materials with promising applications: cyclodextrin-based deep eutectic supramolecular polymers

One‐pot synthesis of pillar[5]quinone‐amine polymer coated silica as stationary phase for high‐performance liquid chromatography

A novel pillar[3]trianglimine macrocycle with a deep cavity used as a chiral selector to prepare a chiral stationary phase by thiol‐ene click reaction for enantioseparation in high‐performance liquid chromatography

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