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

Shi, Ge; Dai, Xiao; Zhou, Yue; Zhang, Jie; Shen, Jun; Wan, Xinhua

doi:10.1039/d0py00205d

Cited by 21 publications

(24 citation statements)

References 44 publications

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“…Shi et al [ 39 ] prepared CSPs based on proline-derived helical poly(phenylacetylene)s ( Figure 2 B) coated on porous silica gel. This type of CSPs presented an advantage of adjusting its resolution ability according with the coating solvent.…”

Section: Coating Methodsmentioning

confidence: 99%

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Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

et al. 2021

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Enantioselective chromatography is one of the most used techniques for the separation and purification of enantiomers. The most important issue for a specific successful enantioseparation is the selection of the suitable chiral stationary phase (CSP). Different synthetic approaches have been applied for the preparation of CSPs, which embrace coating and immobilization methods. In addition to the classical and broadly applied coating and immobilization procedures, innovating strategies have been introduced recently. In this review, an overview of different methods for the preparation of coated and immobilized CSPs is described. Updated examples of CSPs associated with the various strategies are presented. Considering that after the preparation of a CSP its characterization is fundamental, the methods used for the characterization of all the described CSPs are emphasized.

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Section: Coating Methodsmentioning

confidence: 99%

“…For some racemates, the new CSP demonstrated an improved enantioselectivity than the commercials columns CHIRALCEL OD-H ® and CHIRALPAK AD-H ® under the normal-phase elution mode. CSPs characterization was performed by NMR, elemental analysis and Raman measurement [ 39 ].…”

Section: Coating Methodsmentioning

confidence: 99%

Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

et al. 2021

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“…To acquire deep understanding of the chiral biomacromolecules, scientists have synthesized a series of chiral helical polymers and helical architectures imitating the natural counterparts. [ 158,159 ] The typical artificial chiral helical polymers include polyacetylenes, [ 166 ] polyisocyanides, [ 167 ] polycarbodiimides, [ 168 ] poly(quinoxaline‐2,3‐diyl)s, [ 169 ] and others. [ 158,159 ] If combing synthetic helical polymers with graphene, the resulting chiral hybrids may incorporate the respective advantages of chiral polymers and graphene materials.…”

Section: Construction Of Chiral Graphene Hybrid Materialsmentioning

confidence: 99%

Chiral Graphene Hybrid Materials: Structures, Properties, and Chiral Applications

et al. 2021

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Chirality has become an important research subject. The research areas associated with chirality are under substantial development. Meanwhile, graphene is a rapidly growing star material and has hard‐wired into diverse disciplines. Rational combination of graphene and chirality undoubtedly creates unprecedented functional materials and may also lead to great findings. This hypothesis has been clearly justified by the sizable number of studies. Unfortunately, there has not been any previous review paper summarizing the scattered studies and advancements on this topic so far. This overview paper attempts to review the progress made in chiral materials developed from graphene and their derivatives, with the hope of providing a systemic knowledge about the construction of chiral graphenes and chiral applications thereof. Recently emerging directions, existing challenges, and future perspectives are also presented. It is hoped this paper will arouse more interest and promote further faster progress in these significant research areas.

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“…Recently, a series of stereoregular helical polyacetylene derivatives bearing amino acids, amino alcohols, and their phenylcarbamate residues as side chains were synthesized for use as CSPs in HPLC [170][171][172][173][174]., Their structures are presented in Figure 8. The chiral side chain was found to have an important influence on the formation of the main chain helical structure and the chiral recognition capability of the polymer.…”

Section: Synthetic Helical Polymer-based Cspsmentioning

confidence: 99%

“…Optically active polyacetylene derivative 35 showed more extensive chiral selectivity, while optically active polyacetylene derivative 36 showed more specific recognition of certain racemates, such as trans-1,2-cyclohexanedicarboxylic acid dianilide [172]. Moreover, for polymers with phenylcarbamate substituted amino acid side chains (e.g., optically active polyacetylene derivatives 37a-37i), chiral separation performance was largely affected by the type, position, and the number of substituents on the benzene rings [173,174].…”

Section: Synthetic Helical Polymer-based Cspsmentioning

confidence: 99%

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

Zhang

2021

J of Separation Science

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Separations and analyses of chiral compounds are important in many fields, including pharmaceutical production, preparation of chemical intermediates, and biochemistry. High-performance liquid chromatography using a chiral stationary phase is regarded as one of the most valuable methods for enantiomeric separation and analysis because it is highly efficient, is broadly applicable, and has powerful separation capability. The focus for development of this method is the identification of novel chiral stationary phases with superior recognition performance and good stability. The present article reviews recent progress in the development of new chiral stationary phases for high-performance liquid chromatography between January 2018 and June 2021. These newly reported chiral stationary phases are divided into three categories: small organic moleculebased (cyclodextrin and its derivatives, macrocyclic antibiotics, cinchona alkaloids, and other low molecular weight chiral molecules), macromoleculebased (cellulose and amylose derivatives, chitin and chitosan derivatives, and synthetic helical polymers) and chiral porous material-based (chiral metal-organic frameworks, chiral covalent organic frameworks, and chiral inorganic mesoporous silicas). Each type of chiral stationary phase is discussed in detail.

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

Abstract: Proline-derived aliphatically substituted polyacetylenes with stable helical conformations exhibit an excellent enantioseparation ability as chiral stationary phases of HPLC.

Cited by 21 publications

References 44 publications

Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

Chiral Graphene Hybrid Materials: Structures, Properties, and Chiral Applications

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

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