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A Chiral Supramolecular Polymer Membrane with no Chiral Substituents by Highly Selective Photocyclic Aromatization of a One‐Handed Helical Cis ‐ cisoidal Polyphenylacetylene
Author(s) -
Liu Lijia,
Long Qing,
Aoki Toshiki,
Namikoshi Takeshi,
Abe Yunosuke,
Miyata Mari,
Teraguchi Masahiro,
Kaneko Takashi,
Wang Yudan,
Zhang Chunhong
Publication year - 2015
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201400526
Subject(s) - supramolecular chemistry , trimer , chemistry , chirality (physics) , phenylacetylene , stacking , membrane , xylylene , polymer chemistry , hydroxymethyl , helix (gastropod) , polymerization , sulfoxide , hydrogen bond , circular dichroism , supramolecular polymers , polymer , stereochemistry , crystallography , catalysis , molecule , organic chemistry , dimer , crystal structure , chiral symmetry breaking , quark , biochemistry , quantum mechanics , nambu–jona lasinio model , physics , snail , ecology , biology
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.