Simultaneous improvement of permeability and selectivity in enantioselective permeation through solid chiral membranes from a newly synthesized one-handed helical polyphenylacetylene with aldehyde pendant groups by enantioselective reaction

Zang, Yu; Qu, Yanqing; Aoki, Toshiki; Teraguchi, Masahiro; Kaneko, Takashi; Jia, Hongge; Ma, Liqun; Miao, Fengjuan

doi:10.1016/j.polymer.2019.03.039

Cited by 12 publications

(15 citation statements)

References 34 publications

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“…Enantioselective permeation of L-tyrosine was also performed by using a functionalized single-walled carbon nanotube thin-film nanocomposite membrane and D-tryptophan as the chiral probes. 875 In the last few years, functionalized one-handed helical polyacetylenes have been also used as enantioselective membranes for the enantioseparation of phenylethylamine 876,877 and mandelic acid. 878 4.4.2.…”

Section: Enantioselective Adsorption and Permeationmentioning

confidence: 99%

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Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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It is not a coincidence that both chirality and noncovalent interactions are ubiquitous in nature and synthetic molecular systems. Noncovalent interactivity between chiral molecules underlies enantioselective recognition as a fundamental phenomenon regulating life and human activities. Thus, noncovalent interactions represent the narrative thread of a fascinating story which goes across several disciplines of medical, chemical, physical, biological, and other natural sciences. This review has been conceived with the awareness that a modern attitude toward molecular chirality and its consequences needs to be founded on multidisciplinary approaches to disclose the molecular basis of essential enantioselective phenomena in the domain of chemical, physical, and life sciences. With the primary aim of discussing this topic in an integrated way, a comprehensive pool of rational and systematic multidisciplinary information is provided, which concerns the fundamentals of chirality, a description of noncovalent interactions, and their implications in enantioselective processes occurring in different contexts. A specific focus is devoted to enantioselection in chromatography and electromigration techniques because of their unique feature as “multistep” processes. A second motivation for writing this review is to make a clear statement about the state of the art, the tools we have at our disposal, and what is still missing to fully understand the mechanisms underlying enantioselective recognition.

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Section: Enantioselective Adsorption and Permeationmentioning

confidence: 99%

“…In the last few years, functionalized one-handed helical polyacetylenes have been also used as enantioselective membranes for the enantioseparation of phenylethylamine , and mandelic acid …”

Section: Trends In Enantioselective Recognition In Natural and Synthe...mentioning

confidence: 99%

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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“…[9][10][11][12][13][14] In multitudinous synthetic optically active polymers, one-handed helical poly ( phenylacetylene) has attracted extensive attention because of its particular helical structure and properties. [15][16][17][18] In previous studies, we designed and prepared various onehanded helical poly( phenylacetylene) polymers with amino acid groups and their corresponding coated-type CSPs, which demonstrated excellent enantiomer resolution ability. [19][20][21][22][23][24] However, when evaluating the chiral recognition ability of these CSPs, we reported that polymers coated on the silica gel were dissolved or became swollen by certain solvents with a strong dissolving ability, such as chloroform (CHCl 3 ), dichloromethane, and tetrahydrofuran (THF); these solvents greatly limit the choice of eluent and the recycling of CSPs.…”

Section: Introductionmentioning

confidence: 99%

“…9–14 In multitudinous synthetic optically active polymers, one-handed helical poly(phenylacetylene) has attracted extensive attention because of its particular helical structure and properties. 15–18…”

Section: Introductionmentioning

confidence: 99%

Hybridization of helical poly(phenylacetylene)s bearing l-proline tripeptide pendants into porous silica microspheres as a solvent-tolerable chiral stationary phase for liquid chromatography

Huang

Zhou

Zhang

et al. 2023

Analyst

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“…We previously reported some enantioselectively permeable membranes prepared from chiral synthetic polymers. − They were categorized into two types. One was prepared from pure chiral poly(phenylacetylene)s (PPA), and the other was blend membranes consisting of chiral oligomethylpinanylsiloxane (OMPS) as the additive and achiral polymers as supporting membranes .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Well-Defined Chiral Oligopinanylsiloxane Graft Copoly(phenylacetylene)s Using the Macromonomer Method and Their Enantioselective Permeability

Zang

Aoki

Teraguchi

et al. 2020

ACS Appl. Polym. Mater.

Self Cite

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As enantioselectively permeable membrane materials showing high permeability and good self-membrane forming ability, 24 well-defined chiral graft copolymers (PPA-graft-OMPS) consisting of flexible chiral oligomethylpinanylsiloxane (OMPS) grafts and a rigid poly(phenylacetylene) (PPA) backbone were synthesized stepwise in a well-controlled manner. First, synthesized cyclic OMPS monomers containing one or two chiral pinanyl groups were used in living anion ring-opening polymerization to produce the precursors of the corresponding macromonomers whose degrees of polymerization were controlled. Then, by introducing a triple bond at one end of the precursors, the macromonomers were obtained. Finally, PPA-graft-OMPSs with controlled numbers of the grafts were synthesized by copolymerization of the macromonomers with phenylacetylene comonomers. The PPA-graft-OMPSs show good self-membrane forming abilities in spite of the very high content of the flexible OMPS unit because of the rigid conjugated backbone. They show stable enantioselective permeation with high permeability for around 1000 h based on solution selectivity.

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Simultaneous improvement of permeability and selectivity in enantioselective permeation through solid chiral membranes from a newly synthesized one-handed helical polyphenylacetylene with aldehyde pendant groups by enantioselective reaction

Cited by 12 publications

References 34 publications

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Hybridization of helical poly(phenylacetylene)s bearing l-proline tripeptide pendants into porous silica microspheres as a solvent-tolerable chiral stationary phase for liquid chromatography

Synthesis of Well-Defined Chiral Oligopinanylsiloxane Graft Copoly(phenylacetylene)s Using the Macromonomer Method and Their Enantioselective Permeability

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