A quasi-dual-chiral-channel specific enantioseparation material

Lu, Xinling; Li, Yuan; Yang, Jitong; Wang, Yong

doi:10.1016/j.cclet.2023.108342

Cited by 6 publications

(5 citation statements)

References 25 publications

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“…Supramolecular-like cyclodextrins (CDs) have been widely used in enantiomeric separation due to three-dimensional chiral channels. − In our previous study, it was found that methylated cyclodextrin (MCD) has good recognition ability for chiral alcohols and amines . Glutathione (GSH) is a typical tripeptide, which has a good recognition ability for polar chiral compounds such as amino acids and organic acids. , This renders COF great potential for chiral recognition and separation if MCD and GSH can be simultaneously immobilized in the pore of the COF.…”

Section: Resultsmentioning

confidence: 99%

Synergetic Multichiral Covalent Organic Framework for Enantioselective Recognition and Separation

Chen,

Huang,

Xia

et al. 2024

Anal. Chem.

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In enantiomer recognition and separation, a highly enantioselective approach with universal applicability is urgently desired but hard to realize, especially in the case of chiral molecules. To resolve the trade-off between enantioselectivity and universality, a glutathione (GSH) and methylated cyclodextrins (MCD)-functionalized covalent organic framework (GSH-MCD COF) with porosity and abundant chiral surfaces is presented that was designed and synthesized for recognition and separation of various enantiomers. As expected, the GSH-MCD COF can be used as chiral stationary phases for the separation of various enantiomers, including aromatic alcohols, aromatic acids, amides, amino acids, and organic acids, with performance and versatility even superior to some widely used commercial chiral chromatographic columns. Furthermore, the synthesized GSH-MCD COF shows high enantioselectivity for the rapid recognition and identification of enantiomers and chiral metabolites when coupling to Raman spectroscopy. Molecular simulations suggest that the COF provides a confined microenvironment for cyclodextrins and peptides that dictates the separation and recognition capability. This work provides a strategy to synthesize synergetic multichiral COF and achieve separations and recognitions of enantiomers in complex samples.

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Section: Resultsmentioning

confidence: 99%

Synergetic Multichiral Covalent Organic Framework for Enantioselective Recognition and Separation

Chen,

Huang,

Xia

et al. 2024

Anal. Chem.

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“…A "dual" selector for HPLC enantioseparations was constructed by combining the ion-exchange type selector quinine and a lipophilic CD derivative [195]. In this selector, quinine was incorporated in the spacer, which attached a methyl or chlorine substituted per-(phenylcarbamoyl)-β-CD to the solid support.…”

Section: Miscellaneous Selectorsmentioning

confidence: 99%

Update on chiral recognition mechanisms in separation science

Scriba

2024

J of Separation Science

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The stereospecific analysis of chiral molecules is an important issue in many scientific fields. In separation sciences, this is achieved via the formation of transient diastereomeric complexes between a chiral selector and the selectand enantiomers driven by molecular interactions including electrostatic, ion‐dipole, dipole‐dipole, van der Waals or π‐π interactions as well as hydrogen or halogen bonds depending on the nature of selector and selectand. Nuclear magnetic resonance spectroscopy and molecular modeling methods are currently the most frequently applied techniques to understand the selector‐selectand interactions at a molecular level and to draw conclusions on the chiral separation mechanism. The present short review summarizes some of the recent achievements for the understanding of the chiral recognition of the most important chiral selectors combining separation techniques with molecular modeling and/or spectroscopic techniques dating between 2020 and early 2024. The selectors include polysaccharide derivatives, cyclodextrins, macrocyclic glycopeptides, proteins, donor‐acceptor type selectors, ion‐exchangers, crown ethers, and molecular micelles. The application of chiral ionic liquids and chiral deep eutectic solvents, as well as further selectors, are also briefly addressed. A compilation of all published literature on chiral selectors has not been attempted.

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“…25−29 However, underived CDs provide unsatisfactory enantioselectivity as CSPs in HPLC and GC, and the reported CD-based CSPs only form inclusion complexes with specific structures of chiral molecules, resulting in lower selectivity for other structurally diverse chiral compounds. 30,31 Therefore, taking full advantage of CDs and incorporating CDs into stable frameworks to explore new materials as universal CSPs that can be simultaneously used with excellent characteristics for both HPLC and GC have been challenging.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The separation of chiral compounds is a topic of significant interest due to their prevalence in chemistry and pharmacology since chiral compounds often display distinct biological and pharmacological effects. − Among all of the enantioseparation (resolution) methods, gas chromatography (GC) and high-performance liquid chromatography (HPLC) over CSPs have gained immense popularity and are widely regarded as the most effective approaches for the analytical and preparative separations of enantiomers. − Over the last few decades, there has been significant development of diverse chiral selectors, such as antibiotics, , amino acid derivatives, , macrocycles, , polymers, , ionic liquids, − and ligand- and ion-exchange CSPs; − however, there was currently no CSPs that can resolve every kind of chiral molecules. , Cyclodextrins (CDs), which are the most popular GC CSP following methyl ether derivatization, have been widely employed to overcome the challenges encountered in chromatography. − However, underived CDs provide unsatisfactory enantioselectivity as CSPs in HPLC and GC, and the reported CD-based CSPs only form inclusion complexes with specific structures of chiral molecules, resulting in lower selectivity for other structurally diverse chiral compounds. , Therefore, taking full advantage of CDs and incorporating CDs into stable frameworks to explore new materials as universal CSPs that can be simultaneously used with excellent characteristics for both HPLC and GC have been challenging.…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrin Incorporation into Covalent Organic Frameworks Enables Extensive Liquid and Gas Chromatographic Enantioseparations

Yuan,

Wang,

Xiong

et al. 2023

J. Am. Chem. Soc.

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The separation of enantiomers using high-performance chromatography technologies represents great importance and interest. In this aspect, β-cyclodextrin (β-CD) and its derivatives have been extensively studied as chiral stationary phases (CSPs). Nevertheless, β-CD that was immobilized on a traditional matrix often exhibited low stabilities and limited operating ranges. Recently, covalent organic frameworks (COFs) with highly ordered nanopores are emerging as promising CSPs for enantioseparations, but their practical applications are still hampered by the difficulty of monomer and COF synthesis. Herein, two β-CD-driven COFs are synthesized via a fast and facile plasma-induced polymerization combined postsynthesis modification strategy. The precisely defined COF channels enhanced the accessibility of the accommodated β-CD to the analytes and acted as robust protective barriers to safeguard the β-CD from harsh environments. Therefore, the β-CD-modified COFs can be potentially general CSPs for extensive enantioseparation in both gas chromatography and high-performance liquid chromatography, and a wide range of racemates were separated. Compared to the commonly employed commercial chiral columns, these COF-based columns exhibited comparable resolution capability and superior application versatility. This work integrates the advantages and overcomes the defects of COFs and β-CD, thus advancing COFs as platforms for chiral selector modification and giving great promise for practical chromatographic enantioseparation.

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A quasi-dual-chiral-channel specific enantioseparation material

Cited by 6 publications

References 25 publications

Synergetic Multichiral Covalent Organic Framework for Enantioselective Recognition and Separation

Synergetic Multichiral Covalent Organic Framework for Enantioselective Recognition and Separation

Update on chiral recognition mechanisms in separation science

Cyclodextrin Incorporation into Covalent Organic Frameworks Enables Extensive Liquid and Gas Chromatographic Enantioseparations

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