Thioether bridged cationic cyclodextrin stationary phases: Effect of spacer length, selector concentration and rim functionalities on the enantioseparation

Li, Xiaoxuan; Jin, Xuan; Yao, Xiaobin; Ma, Xiaofei; Wang, Yong

doi:10.1016/j.chroma.2016.06.074

Cited by 28 publications

(17 citation statements)

References 36 publications

(18 reference statements)

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“…After vacuum distillation to remove the solvent and unreacted 3,5‐dimethylphenyl isocyanate, the residue was dissolved in ethyl acetate and sodium chloride solution and stirred for 2 h. After filtration, the collected filtrate was evaporated under vacuum and the crude product was purified by silica gel column chromatography to afford mono‐6 A ‐deoxy‐6‐(1‐allylimidazolium)‐per(3,5‐dimethyl)phenylcarbamoylated‐β‐CD chloride. Finally, thiol functionalized silica , azobisisobutyronitrile, and compound 2 were added to methanol. The reaction mixture was stirred at 50°C for 12 h under N 2 .…”

Section: Methodsmentioning

confidence: 99%

“…The designed synthetic route for the SMPhCDCSP is depicted in Figure 3. First, mono-6 A -deoxy-6-(1-allylimidazolium)β-CD was synthesized from β-CD [32,35]. After that, the prepared mono-6 A -deoxy-6-(1-allylimidazolium)-β and phenyl isocyanate in excess amount were dissolved in anhydrous pyridine and the mixture was stirred at 85 • C for 24 h under N 2 .…”

Section: Synthesis Of the Novel Csp By Thiol-ene Click Chemistrymentioning

confidence: 99%

“…to afford mono-6 A -deoxy-6-(1-allylimidazolium)-per(3,5dimethyl)phenylcarbamoylated-β-CD chloride. Finally, thiol functionalized silica [32,35], azobisisobutyronitrile, and compound 2 were added to methanol. The reaction mixture was stirred at 50 • C for 12 h under N 2 .…”

Section: F I G U R E 1 Structures Of Racemates Used In the Current Workmentioning

confidence: 99%

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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

Tang

Sun

et al. 2018

J of Separation Science

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In this work, a novel single sulfoether-bridged cationic per(3,5-dimethyl)phenylcarbamoylated-β-cyclodextrin separation material was prepared by thiol-ene click chemistry and characterized by using FTIR spectroscopy, solid-state C NMR spectroscopy and elemental analysis, which confirmed the correct structure. The separation material exhibited a good achiral separation performance for benzene homologues and phenylamine analogs, especially o-xylene and m-xylene, and m-phenylenediamine and o-phenylenediamine can be discriminated by the (3,5-dimethyl)phenylcarbamoyl cyclodextrins. The chiral resolving ability of the separation material was evaluated by discriminating various isoxazolines, flavonoids, and β-blockers in reversed-phase high-performance liquid chromatography. For isoxazolines, the material showed the best chiral discrimination toward 3-aryl-5-(2-oxopyrrolidin-1-yl)-isoxazolines, where the resolution for 3ClPh-OPr reached 6.03. For flavonoids, it exhibited more efficient separation to the ones with more hydrophobic substituents, with a resolution of 5.93 for 6-hydroxyflavanone. β-Blockers were also enantioseparated satisfactorily on the material. The as-prepared separation material is a good member of the thiol-ene click derived cyclodextrin stationary phase family.

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Section: Methodsmentioning

confidence: 99%

Section: Synthesis Of the Novel Csp By Thiol-ene Click Chemistrymentioning

confidence: 99%

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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

Tang

Sun

et al. 2018

J of Separation Science

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“…Apart from the special structure, the hydroxyl groups on CD rims offer the possibility of modification. Owing to these superiorities, CDs are widely applied in various separation technologies , especially in HPLC . The development of CD‐chiral stationary phases (CSPs) mainly focuses on two terms: CD functionalization and spacer design .…”

Section: Introductionmentioning

confidence: 99%

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

Jin

Wang

2019

Electrophoresis

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In this study, a series of novel CD chiral stationary phases were fabricated by immobilization of mono‐6A‐deoxy‐N3‐cyclodextrin onto silica surfaces followed by click regulation of CD primary face with 4‐pentynoic acid (acidic moiety), 2‐propynylamine (alkaline moiety) and L‐propargylglycine (chiral amino acid moiety), respectively. Enantioseparations of various kinds of racemates including dansyl‐amino acids, chiral lactides and diketones were conducted in reversed phase modes on these chiral stationary phases, where nearly forty diketones and chiral lactides were firstly separated on cyclodextrin stationary phases. 4‐Pentynoic acid moiety can make the retention ability decline while amine moiety significantly enhanced the retention ability of the stationary phases. For most of the studied analytes, the chiral amino acid moiety had the most positive effects on both the retention time and the resolution. The inclusion complexation between chiral analytes and cyclodextrins were also investigated by fluorescence method.

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“…As the second generation of supramolecular compounds, cyclodextrins (CDs) are known to embody a unique hydrophobic inner cavity and a hydrophilic surface—originating from the hydroxyl moieties on the rims [ 6 , 7 ]. CDs show an exceptional ability to selectively bind suitably-sized aliphatic and aromatic molecules to form inclusion complexes [ 8 , 9 ]. This demonstrates great potential in various applications, such as sensing, catalysis, separation, adsorption, and the removal of organic pollutants from contaminated water [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

Click Access to a Cyclodextrin-Based Spatially Confined AIE Material for Hydrogenase Recognition

Zhao

Wang

et al. 2018

Sensors

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The spatial confinement of conjugated phenyl rotators is a compulsory requirement for the fluorescence enhancement of aggregation induced emission (AIE) molecules. This work reports a novel spatially confined AIE material by restricting several tetraphenylethylene (TPE) molecules around the primary face of β-cyclodextrin (CD) via a Cu(I) catalytic 1,3-dipolar cycloaddition reaction (click chemistry). The spatial confinement effect was found to significantly enhance the fluorescence emission when compared with a single TPE modified CD. In addition, the emission maxima took place with the dimethyl sulfoxide volume ratio of 30% in a water mixture, which is remarkably different from traditional AIE molecules. Benefiting from the CD’s complexation effect, this material exhibits a selective fluorescence quenching property in certain hydrogenases and can be used as a fluorescence probe for hydrogenase sensing. This demonstrates the potential of the spatially confined AIECD for practical applications.

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Thioether bridged cationic cyclodextrin stationary phases: Effect of spacer length, selector concentration and rim functionalities on the enantioseparation

Cited by 28 publications

References 36 publications

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

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

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

Click Access to a Cyclodextrin-Based Spatially Confined AIE Material for Hydrogenase Recognition

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