Reversible Stereoselective Folding/Unfolding Fueled by the Interplay of Photoisomerism and Hydrogen Bonding | Zendy

Opie Christopher R. | Zendy; Kumagai Naoya | Zendy; Shibasaki Masakatsu | Zendy

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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 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.201610279

Subject(s) - moiety , intramolecular force , stereocenter , hydrogen bond , stereoselectivity , folding (dsp implementation) , chemistry , azobenzene , sum frequency generation spectroscopy , stereochemistry , crystallography , molecule , organic chemistry , sum frequency generation , physics , catalysis , engineering , nonlinear system , quantum mechanics , nonlinear optics , electrical engineering , enantioselective synthesis

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.

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