Integration of the 1,2,3-Triazole "Click" Motif as a Potent Signalling Element in Metal Ion Responsive Fluorescent Probes

In a systematic approach we synthesized a new series of fluorescent probes incorporating donor–acceptor (D‐A) substituted 1,2,3‐triazoles as conjugative π‐linkers between the alkali metal ion receptor N‐phenylaza‐[18]crown‐6 and different fluorophoric groups with different electron‐acceptor properti...

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Veröffentlicht in:	Chemistry : a European journal Jg. 19; H. 9; S. 2990 - 3005
Hauptverfasser:	Ast, Sandra, Fischer, Tobias, Müller, Holger, Mickler, Wulfhard, Schwichtenberg, Mathias, Rurack, Knut, Holdt, Hans-Jürgen
Format:	Journal Article
Sprache:	Englisch
Veröffentlicht:	Weinheim WILEY-VCH Verlag 25.02.2013 WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc
Schlagworte:	Acetonitrile Alkali metals Anthracene charge transfer Chemical compounds Chemistry Chemistry, Multidisciplinary click chemistry Electrochemistry Electron transfer Fluorescence fluorescent probes Ions Mathematical analysis Metal ions Physical Sciences Physiology Precursors Probes Receptors Science & Technology Signalling AZACROWN ETHER DYES WURSTERS CROWNS click chemistry CATION COMPLEXATION PHOTOPHYSICAL PROPERTIES SPECTRAL PROPERTIES SENSORS metal ions charge transfer fluorescent probes INTRAMOLECULAR CHARGE-TRANSFER electron transfer NEAR-INFRARED NIR ENERGY-TRANSFER
ISSN:	0947-6539, 1521-3765, 1521-3765
Online-Zugang:	Volltext
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Zusammenfassung:	In a systematic approach we synthesized a new series of fluorescent probes incorporating donor–acceptor (D‐A) substituted 1,2,3‐triazoles as conjugative π‐linkers between the alkali metal ion receptor N‐phenylaza‐[18]crown‐6 and different fluorophoric groups with different electron‐acceptor properties (4‐naphthalimide, meso‐phenyl‐BODIPY and 9‐anthracene) and investigated their performance in organic and aqueous environments (physiological conditions). In the charge‐transfer (CT) type probes 1, 2 and 7, the fluorescence is almost completely quenched by intramolecular CT (ICT) processes involving charge‐separated states. In the presence of Na+ and K+ ICT is interrupted, which resulted in a lighting‐up of the fluorescence in acetonitrile. Among the investigated fluoroionophores, compound 7, which contains a 9‐anthracenyl moiety as the electron‐accepting fluorophore, is the only probe which retains light‐up features in water and works as a highly K+/Na+‐selective probe under simulated physiological conditions. Virtually decoupled BODIPY‐based 6 and photoinduced electron transfer (PET) type probes 3–5, where the 10‐substituted anthracen‐9‐yl fluorophores are connected to the 1,2,3‐triazole through a methylene spacer, show strong ion‐induced fluorescence enhancement in acetonitrile, but not under physiological conditions. Electrochemical studies and theoretical calculations were used to assess and support the underlying mechanisms for the new ICT and PET 1,2,3‐triazole fluoroionophores. Light up: Combination of a typical alkali‐metal ion receptor with various popular fluorophores in different signalling architectures through simple clicking of the modular precursors yields probes that integrate a new donor–acceptor‐substituted 1,2,3‐triazole motif, which gives rise to interesting absorption and fluorescence responses upon target binding.
Bibliographie:	istex:0003351ADC5E43A8772CC2CEE0217B187A4A7DDB DFG - No. GRK 837 ark:/67375/WNG-B19V4XXM-H ArticleID:CHEM201201575 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
ISSN:	0947-6539 1521-3765 1521-3765
DOI:	10.1002/chem.201201575