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

Authors

  • Dr. Sandra Ast,

    1. Institut für Chemie, Anorganische Chemie, Universität Potsdam, Karl-Liebknecht Str. 24–25, 14467 Golm (Germany), Fax: (+49) 331-977-5055
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  • Tobias Fischer,

    1. Fachbereich 1.9 Sensormaterialien, BAM Bundesanstalt für Materialforschung und -prüfung Richard-Willstätter Str. 11, 12489 Berlin (Germany)
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  • Holger Müller,

    1. Institut für Chemie, Anorganische Chemie, Universität Potsdam, Karl-Liebknecht Str. 24–25, 14467 Golm (Germany), Fax: (+49) 331-977-5055
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  • Dr. Wulfhard Mickler,

    1. Institut für Chemie, Anorganische Chemie, Universität Potsdam, Karl-Liebknecht Str. 24–25, 14467 Golm (Germany), Fax: (+49) 331-977-5055
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  • Mathias Schwichtenberg,

    1. Institut für Chemie, Anorganische Chemie, Universität Potsdam, Karl-Liebknecht Str. 24–25, 14467 Golm (Germany), Fax: (+49) 331-977-5055
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  • Dr. Knut Rurack,

    Corresponding author
    1. Fachbereich 1.9 Sensormaterialien, BAM Bundesanstalt für Materialforschung und -prüfung Richard-Willstätter Str. 11, 12489 Berlin (Germany)
    • Fachbereich 1.9 Sensormaterialien, BAM Bundesanstalt für Materialforschung und -prüfung Richard-Willstätter Str. 11, 12489 Berlin (Germany)
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  • Prof. Dr. Hans-Jürgen Holdt

    Corresponding author
    1. Institut für Chemie, Anorganische Chemie, Universität Potsdam, Karl-Liebknecht Str. 24–25, 14467 Golm (Germany), Fax: (+49) 331-977-5055
    • Institut für Chemie, Anorganische Chemie, Universität Potsdam, Karl-Liebknecht Str. 24–25, 14467 Golm (Germany), Fax: (+49) 331-977-5055
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Abstract

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 35, 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.

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