A Chiral Supramolecular Polymer Membrane with no Chiral Substituents by Highly Selective Photocyclic Aromatization of a One-Handed Helical Cis-cisoidal Polyphenylacetylene

摘要

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 pi-pi stacking are thought to contribute to the retention of the chirality during the two-step reaction in the membrane state.