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Synthesis and chiral recognition ability of helical polyacetylenes bearing helicene pendants

Abstract : Novel polyacetylenes bearing an optically active or racemic [6]helicene unit as the pendant groups directly bonded to the main-chain (poly-1s) were prepared by the polymerization of the corresponding acetylenes (1-rac, 1-P, and 1-M) with a rhodium catalyst. The optically active polyacetylenes (poly-1-P and poly-1-M) formed a preferred-handed helical conformation biased by the optically active helicene pendants, resulting in the induced circular dichroism (ICD) in their π-conjugated polymer backbone regions. The optically active helical polymers, when employed as an enantioselective adsorbent, showed a high chiral recognition ability towards racemates, such as the monomeric [6]helicene and 1,1’-binaphthyl analogues, and enantioselectively adsorbed one of the enantiomers.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01082742
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Submitted on : Friday, November 14, 2014 - 11:30:35 AM
Last modification on : Thursday, March 5, 2020 - 2:04:37 PM
Long-term archiving on: : Friday, April 14, 2017 - 1:27:53 PM

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Emmanuel Anger, Hiroki Iida, Tomoko Yamaguchi, Koutarou Hayashi, Daisuke Kumano, et al.. Synthesis and chiral recognition ability of helical polyacetylenes bearing helicene pendants. Polymer Chemistry, Royal Society of Chemistry - RSC, 2014, 5 (17), pp.4909-4914. ⟨10.1039/C4PY00692E⟩. ⟨hal-01082742⟩

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