Synthesis of a poly(diphenylacetylene) bearing optically active anilide pendants and its application to a chiral stationary phase for high-performance liquid chromatography

Nozaki, Mai; Hirose, Daisuke; Maeda, Katsuhiro

doi:10.1016/j.chroma.2020.461173

Cited by 18 publications

(18 citation statements)

References 41 publications

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“…Another interesting family of helical polymers are the poly(diphenylacetylene)s (PDPAs) [71–93] that resemble PPAs in the main chain, which in both cases is made up of conjugated double bonds. However, the presence of a phenyl group on each carbon of the double bond in PDPAs makes the properties of both materials very different.…”

Section: Introductionmentioning

confidence: 99%

Dissymmetric Chiral Poly(diphenylacetylene)s: Secondary Structure Elucidation and Dynamic Luminescence

et al. 2022

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The secondary structure of a dissymmetric and chiral poly(diphenylacetylene) (PDPA) is elucidated by combining the data from NMR experiments (regioregular head to tail structure), Raman and IR studies (E configuration of the polyene double bonds), and high-resolution AFM images (helical pitch, packing angle and orientation of the external helix). As a result, an E-transoidal polyene backbone describing three coaxial helices is obtained. Theoretical electronic circular dichroism (ECD) studies of the structure show a good correspondence between experimental and theoretical data and allow one to decipher that the first Cotton band is generated by the poly(diphenylacetylene) core and not only by the polyene backbone. The dynamic behavior of poly-(S)-2 is also demonstrated by a helix inversion effect produced by conformational changes at the pendant groups when annealed in solvents with different donor abilities. This phenomenon is accompanied by an inversion of the circular polarized luminescence of the PDPA (CPL switch).

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Section: Introductionmentioning

confidence: 99%

Dissymmetric Chiral Poly(diphenylacetylene)s: Secondary Structure Elucidation and Dynamic Luminescence

et al. 2022

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“…The same group also introduced new poly(diphenylacetylene)-based CSPs with optically active anilide pendants, which were bonded by using EDC as a coupling agent [ 67 ]. The presence of macromolecular helicity in the polymeric backbone induced during the synthesis of one CSP contributed towards an enhanced enantiorecognition ability.…”

Section: Immobilization Methodsmentioning

confidence: 99%

“…The presence of macromolecular helicity in the polymeric backbone induced during the synthesis of one CSP contributed towards an enhanced enantiorecognition ability. NMR, elemental analysis and TGA were applied for CSP characterization [ 67 ].…”

Section: Immobilization Methodsmentioning

confidence: 99%

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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“…Synthetic helical polymers have been widely used as CSPs for HPLC separation of racemic compounds and some of them have been commercialized. However, the helicity and stereoregularity of the polymer backbone, which are affected by factors such as temperature, solvent, additives, and side-chain group, significantly impact chiral separation [178][179][180][181][182].…”

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 of a poly(diphenylacetylene) bearing optically active anilide pendants and its application to a chiral stationary phase for high-performance liquid chromatography

Cited by 18 publications

References 41 publications

Dissymmetric Chiral Poly(diphenylacetylene)s: Secondary Structure Elucidation and Dynamic Luminescence

Dissymmetric Chiral Poly(diphenylacetylene)s: Secondary Structure Elucidation and Dynamic Luminescence

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

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

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