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A Chiroptical Molecular Switch with Distinct Chiral and Photochromic Entities and Its Application in Optical Switching of a Cholesteric Liquid Crystal
Author(s) -
Delden Richard A. van,
Mecca Tommaso,
Rosini Carlo,
Feringa Ben L.
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200305276
Subject(s) - photochromism , cholesteric liquid crystal , molecular switch , liquid crystal , liquid crystalline , optical switch , materials science , chirality (physics) , chemistry , nanotechnology , optoelectronics , organic chemistry , molecule , chiral symmetry , physics , quantum mechanics , quark , nambu–jona lasinio model
Two new structurally related photoswitches are described, in which azobenzene photochromism is combined with the chirality of a 2,2′‐dihydroxy‐1,1′‐binaphthyl unit. In system 1 the chiral binaphthyl moiety is bridged by a methylene tether, locking the biaryl chirality while in system 2 the biaryl core is unbridged and has considerable conformational flexibility. Both compound are capable of inducing cholesteric liquid crystalline phases and proved to be good photoswitches both in solution and in a liquid crystalline matrix. Compound 2 is capable of completely reversing the liquid crystalline chirality which is unique for a chiroptical molecular switch where the switching unit and the chiral moiety are separate entities.