A Chiral Supramolecular Polymer Membrane with no Chiral Substituents by Highly Selective Photocyclic Aromatization of a One‐Handed Helical Cis‐cisoidal Polyphenylacetylene. Issue 5 (3rd December 2014)

• Record Type: Journal Article
• Authors: Liu, Lijia; Long, Qing; Aoki, Toshiki; Namikoshi, Takeshi; Abe, Yunosuke; Miyata, Mari; Teraguchi, Masahiro; Kaneko, Takashi; Wang, Yudan; Zhang, Chunhong
• Is Part Of: Macromolecular chemistry and physics. Volume 216:Issue 5(2015:Mar.)
• Page Start: 530
• Page End: 537
• Publication Date: 2014-12-03
• Subjects: Polymers -- Periodicals; Polymerization -- Periodicals; Synthetic products -- Periodicals; Macromolecules -- Periodicals; 547.7
• DOI: 10.1002/macp.201400526
• Languages: English
• ISSNs: 1022-1352

Abstract

<abstract abstract-type="main" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p>A one‐handed helical <italic>cis‐cisoidal</italic> polyphenylacetylene (<bold>P</bold>) is successfully synthesized by an asymmetric‐induced polymerization of a chiral‐substituted phenylacetylene having two hydroxymethyl groups. Quantitative photocyclic aromatization of <bold>P</bold> in a membrane‐state followed by in situ removal of the chiral substituents affords a one‐handed helical supramolecular polymer membrane of the corresponding cyclic trimer (<bold>T)</bold> with no chiral substituents. The original one‐handed helicity of the precursor <bold>P</bold> is successfully transmitted to the resulting supra­molecular helicity of <italic>de</italic>‐<bold>T</bold>. Both the hydrogen bonds and the π–π stacking are thought to contribute to the retention of the chirality during the two‐step reaction in the membrane state. <boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgj433860v" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>