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Reversible Stereoselective Folding/Unfolding Fueled by the Interplay of Photoisomerism and Hydrogen Bonding
Author(s) -
Opie Christopher R.,
Kumagai Naoya,
Shibasaki Masakatsu
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201610279
Subject(s) - moiety , intramolecular force , stereocenter , hydrogen bond , chemistry , stereoselectivity , folding (dsp implementation) , azobenzene , sum frequency generation spectroscopy , nuclear magnetic resonance spectroscopy , stereochemistry , crystallography , molecule , organic chemistry , enantioselective synthesis , sum frequency generation , physics , engineering , nonlinear system , quantum mechanics , nonlinear optics , electrical engineering , catalysis
A linear molecular architecture equipped with complementary three‐fold hydrogen‐bonding units embedded with a photoswitchable trans ‐tetrafluoroazobenzene moiety was synthesized. The trans to cis photoisomerism of the azobenzene unit induced drastic changes in the molecular architecture as a result of intramolecular hydrogen bonding as evidenced by NMR spectroscopy and size exclusion chromatography. A minute stereogenic element in the linear trans state enabled stereoselective folding into the cis state, thus producing a globular architecture with enhanced chiroptical property.