Influence of Helical Structure on Chiral Recognition of Poly(phenylacetylene)s Bearing Phenylcarbamate Residues of <scp>L</scp>‐Phenylglycinol and Amide Linage as Pendants

Zhang, Chunhong; Ma, Rui; Wang, Hailun; Sakai, Ryosuke; Satoh, Toshifumi; Kakuchi, Toyoji; Liu, Lijia

doi:10.1002/chir.22453

Cited by 18 publications

(7 citation statements)

References 31 publications

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“…Analogous helical PPAs bearing l -phenylglycinol and its phenylcarbamate derivatives as pendants ( 656 and 657 ) have also been prepared. , The resolution abilities of 657 are significantly influenced by the substituents on the phenylcarbamate groups when used as a CSP, and 657e with the 3,5-dichloro substituents exhibits a higher recognition ability than the others and can achieve complete resolutions of several enantiomers, including 658 (Figure B). This is probably due to the more acidic N–H protons of the 3,5-dichlorophenylcarbamate residues, which likely act as the attractive interaction sites with the racemates through hydrogen bonding.…”

Section: Helical Polymers and Their Assembliesmentioning

confidence: 99%

Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

et al. 2016

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In this review, we describe the recent advances in supramolecular helical assemblies formed from chiral and achiral small molecules, oligomers (foldamers), and helical and nonhelical polymers from the viewpoints of their formations with unique chiral phenomena, such as amplification of chirality during the dynamic helically assembled processes, properties, and specific functionalities, some of which have not been observed in or achieved by biological systems. In addition, a brief historical overview of the helical assemblies of small molecules and remarkable progress in the synthesis of single-stranded and multistranded helical foldamers and polymers, their properties, structures, and functions, mainly since 2009, will also be described.

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Section: Helical Polymers and Their Assembliesmentioning

confidence: 99%

Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

et al. 2016

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“…Optically active poly(phenylacetylene)s with a preferred-handed helicity have been prepared [16] and some of these systems have been reported to exhibit good chiral recognition abilities as CSPs for HPLC because of their preferred-handed helical conformation [17][18][19][20][21][22][23][24][25][26]. However, very few optically active poly(diphenylacetylene)s have been prepared to date, which has limited research towards evaluating the scope and efficiency of the chiral recognition abilities of these materials [27][28][29][30][31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Optically Active Poly(diphenylacetylene)s Using Polymer Reactions and an Evaluation of Their Chiral Recognition Abilities as Chiral Stationary Phases for HPLC

et al. 2016

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A series of optically active poly(diphenylacetylene) derivatives bearing a chiral substituent (poly-2S) or chiral and achiral substituents (poly-(2S x -co-3 1−x )) on all of their pendant phenyl rings were synthesized by the reaction of poly(bis(4-carboxyphenyl)acetylene) with (S)-1-phenylethylamine ((S)-2) or benzylamine (3) in the presence of a condensing reagent. Their chiroptical properties and chiral recognition abilities as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) were investigated. Poly-2S and poly-(2S x -co-3 1−x ) (0.06 < x < 0.71) formed a preferred-handed helical conformation with opposite helical senses after thermal annealing despite possessing the same chiral pendant (h-poly-2S and h-poly-(2S x -co-3 1−x )). Furthermore, h-poly-2S and h-poly-(2S 0.36 -co-3 0.64 ) emitted circularly polarized luminescence with opposite signs. h-Poly-2S showed higher chiral recognition abilities toward a larger number of racemates than poly-2S without a preferred-handed helicity and the previously reported preferred-handed poly(diphenylacetylene) derivative bearing the same chiral substituent on half of its pendant phenyl rings. h-Poly-(2S 0.36 -co-3 0.64 ) also exhibited good chiral recognition abilities toward several racemates, though the elution order of some enantiomers was reversed compared with h-poly-2S.

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“…Since this discovery, a number of helical polymer-based CSPs have been developed because the one-handed helical structure appears to play an essential role in achieving the high-resolution abilities as CSPs for HPLC [1,4,87,91,92]. Helical polyacetylenes possessing optically active pendants (42)(43)(44) also have been prepared, and some of them exhibit good chiral recognition abilities as CSPs for HPLC because of their preferred-handed helical conformation [26,[93][94][95][96][97][98][99][100][101].…”

Section: Application Of Helical Polyacetylenes As Chiral Materialsmentioning

confidence: 99%

Helical Polyacetylenes Induced via Noncovalent Chiral Interactions and Their Applications as Chiral Materials

Maeda

Yashima

2017

Topics in Current Chemistry Collections

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Construction of predominantly one-handed helical polyacetylenes with a desired helix sense utilizing noncovalent chiral interactions with nonracemic chiral guest compounds based on a supramolecular approach is described. As with the conventional dynamic helical polymers possessing optically active pendant groups covalently bonded to the polymer chains, this noncovalent helicity induction system can show significant chiral amplification phenomena, in which the chiral information of the nonracemic guests can transfer with high cooperativity through noncovalent bonding interactions to induce an almost single-handed helical conformation in the polymer backbone. An intriguing ''memory effect'' of the induced macromolecular helicity is observed for some polyacetylenes, which means that the helical conformations induced in dynamic helical polyacetylene can be transformed into metastable static ones by tuning their helix-inversion barriers. Potential applications of helical polyacetylenes with controlled helix sense constructed by the ''noncovalent helicity induction and/or memory effect'' as chiral materials are also described.

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Influence of Helical Structure on Chiral Recognition of Poly(phenylacetylene)s Bearing Phenylcarbamate Residues of L‐Phenylglycinol and Amide Linage as Pendants

Cited by 18 publications

References 31 publications

Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

Synthesis of Optically Active Poly(diphenylacetylene)s Using Polymer Reactions and an Evaluation of Their Chiral Recognition Abilities as Chiral Stationary Phases for HPLC

Helical Polyacetylenes Induced via Noncovalent Chiral Interactions and Their Applications as Chiral Materials

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