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Enantiodifferentiating Photodimerization of a 2,6‐Disubstituted Anthracene Assisted by Supramolecular Double‐Helix Formation with Chiral Amines
Author(s) -
Urushima Akio,
Taura Daisuke,
Tanaka Makoto,
Horimoto Naomichi,
Tanabe Junki,
Ousaka Naoki,
Mori Tadashi,
Yashima Eiji
Publication year - 2020
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.201916103
Subject(s) - circular dichroism , chemistry , anthracene , chirality (physics) , helix (gastropod) , stereochemistry , supramolecular chemistry , enantiomer , stacking , enantiomeric excess , enantioselective synthesis , crystallography , photochemistry , organic chemistry , crystal structure , catalysis , biology , ecology , chiral symmetry breaking , physics , quantum mechanics , snail , nambu–jona lasinio model , quark
A novel 2,6‐anthrylene‐linked bis( m ‐terphenylcarboxylic acid) strand ( 1 ) self‐associates into a racemic double‐helix. In the presence of chiral mono‐ and diamines, either a right‐ or left‐handed double‐helix was predominantly induced by chiral amines sandwiched between the carboxylic acid strands with accompanying stacking of the two prochiral anthracene linker units in an enantiotopic face‐selective way, as revealed by circular dichroism and NMR spectral analyses. The photoirradiation of the optically active double helices complexed with chiral amines proceeded in a diastereo‐ ( anti or syn ) and enantiodifferentiating way to afford the chiral anti ‐photodimer with up to 98 % enantiomeric excess when ( R )‐phenylethylamine was used as a chiral double‐helix inducer. The resulting optically active anti ‐photodimer can recognize the chirality of amines and diastereoselectively complex with chiral amines.