A Chiral Supramolecular Polymer Membrane with no Chiral Substituents by Highly Selective Photocyclic Aromatization of a One‐Handed Helical <i>Cis</i>‐<i>cisoidal</i> Polyphenylacetylene

Abstract

A one‐handed helical cis‐cisoidal polyphenylacetylene ( P ) is successfully synthesized by an asymmetric‐induced polymerization of a chiral‐substituted phenylacetylene having two hydroxymethyl groups. Quantitative photocyclic aromatization of P 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 ( T) with no chiral substituents. The original one‐handed helicity of the precursor P is successfully transmitted to the resulting supra­molecular helicity of de ‐ T . 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. image