Open AccessSynthesis and Photochromic Properties of Configurationally Varied Azobenzene Glycosides
Author(s) -
Chandrasekaran Vijayanand,
Johannes Eugen,
Kobarg Hauke,
Sönnichsen Frank D.,
Lindhorst Thisbe K.
Publication year - 2014
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201402016
Subject(s) - azobenzene , photochromism , isomerization , moiety , chemistry , conjugated system , glycoside , photoisomerization , photochemistry , stereochemistry , organic chemistry , molecule , catalysis , polymer
Invited for this months cover is the group of Prof. Thisbe K. Lindhorst from Christiana Albertina University of Kiel, Germany. The cover picture shows the principal structures of the azobenzene glycosides, which were synthesized in this work using glycosylation for preparation of the 1,2‐ trans glycosides and Mills reaction for azobenzene coupling (as indicated by the retrosynthetic pair of scissors). Irradiation of these glycoconjugates effects E → Z isomerization of the azobenzene N=N double bond, thus causing a significant change of the relative spatial orientation of the conjugated sugar moiety. The photochromic properties of these ‘sweet switches’ were systematically investigated. For more details, see the Full Paper on 10.1002/open.201402010 (p. 99 ff.)