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• W2017754114 abstract "Message received! Biconformational perhydroanthracenes with bipyridine receptors and pyrene effectors (see figure) have been synthesized and successfully used for signal transduction through conformational transmission. Upon binding of a zinc(II) ion at the bipyridine receptor site a fluorescence signal is generated at the pyrene effector site. 2,3,6,7-Tetrasubstituted cis-anti-cis perhydroanthracenes have been studied as conformational transducers for molecular signal transduction. 2,2′-Bipyridine groups attached to the perhydroanthracene through ether linkages were chosen as receptor substituents, while pyrene groups were selected as effectors. A chelation-induced triple ring flip of the perhydroanthracene could be achieved by the complexation of zinc(II) ions at the bipyridine sites of ligands 13 and 15. It was found that two pyrene substituents attached to the perhydroanthracene via a linker with an E double bond and an ester group could be used to monitor the triple ring flip. In the equatorial positions, the pyrenes are sufficiently close to form an excimer in the excited state, giving a fluorescence signal at 480 nm. In the axial positions, they are far away from each other and give mainly a monomer fluorescence signal at 380 nm. Both the bipyridine receptor and the pyrene effector are present in compound 33. The conformational switching 34→35 (the two conformers of 33) has successfully been used for a signal transduction over a signal distance of 2 nm. 2,3,6,7-Tetrasubstituierte cis-anti-cis Perhydroanthracene eignen sich als konformationelle Signalüberträger zur molekularen Signaltransduktion. 2,2′-Bipyridine, die über eine Etherbrücke mit dem Perhydroanthracen verbunden sind, wurden hierzu als Rezeptorsubstituenten ausgewählt. Ein Chelat-induzierter Tripel-Ring-Flip des Perhydroanthracens ließ sich mit den Verbindungen 13 und 15 durch Bildung eines Zink–Bipyridin Komplexes erreichen. Pyrene können dann als Effektoren verwendet werden, wenn sie eine E-Doppelbindung und einen Ester als Verknüpfungselement zum Perhydroanthracen aufweisen. In den equatorialen Positionen sind die Pyrene nahe genug beieinander, um im angeregten Zustand ein Excimer mit einer Fluoreszenz von 480 nm zu bilden. In den axialen Positionen sind beide Pyrene räumlich so weit voneinander entfernt, daß sie überwiegend eine Monomerfluoreszenz bei 380 nm zeigen. Verbindung 33 wurde hergestellt, bei der der Bipyridin-Rezeptor und der Pyreneffektor zusammen in einem Molekül integriert sind. Über das durch ein Zink-Signal ausgelöste konformationelle Umschalten 34→35 konnte eine erfolgreiche Signaltransduktion über eine Signaldistanz von 2 nm durchgeführt werden. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2111/2001/f2778_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article." @default.
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• W2017754114 date "2001-05-18" @default.
• W2017754114 modified "2023-09-27" @default.
• W2017754114 title "Molecular Signal Transduction by Conformational Transmission: Use of Tetrasubstituted Perhydroanthracenes as Transducers" @default.
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• W2017754114 doi "https://doi.org/10.1002/1521-3765(20010518)7:10<2075::aid-chem2075>3.0.co;2-1" @default.
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