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Issue 17, 2014
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Synthesis and chiral recognition ability of helical polyacetylenes bearing helicene pendants

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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 polymerisation of the corresponding acetylenes (1-rac, 1-P and 1-M) using 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.

Graphical abstract: Synthesis and chiral recognition ability of helical polyacetylenes bearing helicene pendants

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Supplementary files

Article information


Submitted
19 May 2014
Accepted
07 Jun 2014
First published
09 Jun 2014

This article is Open Access

Polym. Chem., 2014,5, 4909-4914
Article type
Paper

Synthesis and chiral recognition ability of helical polyacetylenes bearing helicene pendants

E. Anger, H. Iida, T. Yamaguchi, K. Hayashi, D. Kumano, J. Crassous, N. Vanthuyne, C. Roussel and E. Yashima, Polym. Chem., 2014, 5, 4909
DOI: 10.1039/C4PY00692E

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