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Autoamplification of Molecular Chirality through the Induction of Supramolecular Chirality
Author(s) -
van Dijken Derk Jan,
Beierle John M.,
Stuart Marc C. A.,
Szymański Wiktor,
Browne Wesley R.,
Feringa Ben L.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201311160
Subject(s) - diarylethene , chirality (physics) , ring (chemistry) , supramolecular chemistry , supramolecular chirality , enantiomer , asymmetric induction , photochromism , planar chirality , chemistry , molecule , stereochemistry , materials science , photochemistry , crystallography , enantioselective synthesis , catalysis , organic chemistry , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
The novel concept for the autoamplification of molecular chirality, wherein the amplification proceeds through the induction of supramolecular chirality, is presented. A solution of prochiral, ring‐open diarylethenes is doped with a small amount of their chiral, ring‐closed counterpart. The molecules co‐assemble into helical fibers through hydrogen bonding and the handedness of the fibers is biased by the chiral, ring‐closed diarylethene. Photochemical ring closure of the open diarylethene yields the ring‐closed product, which is enriched in the template enantiomer.