2016
DOI: 10.3390/molecules21111487
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Synthesis of Optically Active Poly(diphenylacetylene)s Using Polymer Reactions and an Evaluation of Their Chiral Recognition Abilities as Chiral Stationary Phases for HPLC

Abstract: 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)… Show more

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Cited by 40 publications
(32 citation statements)
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“…Inspired by the sophisticated functions of biological helical polymers and their assemblies, a rich variety of artificial helical polymers has been prepared over the past decades in order to develop advanced chiral materials for the resolution of enantiomers by chromatography, sensing of chiral molecules, and circularly polarized luminescence . The application of optically active helical polymers for asymmetric catalysis has also attracted growing interest, because a one‐handed helical chirality can significantly contribute to the enantioselectivity due to a one‐handed helical arrangement of the catalytically active, chiral/achiral units along the one‐handed helical polymer backbone .…”
Section: Introductionmentioning
confidence: 99%
“…Inspired by the sophisticated functions of biological helical polymers and their assemblies, a rich variety of artificial helical polymers has been prepared over the past decades in order to develop advanced chiral materials for the resolution of enantiomers by chromatography, sensing of chiral molecules, and circularly polarized luminescence . The application of optically active helical polymers for asymmetric catalysis has also attracted growing interest, because a one‐handed helical chirality can significantly contribute to the enantioselectivity due to a one‐handed helical arrangement of the catalytically active, chiral/achiral units along the one‐handed helical polymer backbone .…”
Section: Introductionmentioning
confidence: 99%
“…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%
“…The direct separation of enantiomers by high‐performance liquid chromatography (HPLC) has become one of the most effective method to give pure isomers . This technique is based on the chiral recognition ability of chiral stationary phases (CSPs) . In spite of polysaccharide‐based CSPs that showed good chiral separation abilities for varies of enantiomers, synthetic helical polymers, especially poly(phenylacetylene) derivatives, have also been widely investigated by researchers around the world because of their specific architectures …”
Section: Introductionmentioning
confidence: 99%