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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| Vydáno v: | Chemistry : a European journal Ročník 19; číslo 9; s. 2990 - 3005 |
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| Hlavní autoři: | , , , , , , |
| Médium: | Journal Article |
| Jazyk: | angličtina |
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Weinheim
WILEY-VCH Verlag
25.02.2013
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
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| ISSN: | 0947-6539, 1521-3765, 1521-3765 |
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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 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. |
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| AbstractList | 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. In a systematic approach we synthesized a new series of fluorescent probes incorporating donoracceptor (D-A) substituted 1,2,3-triazoles as conjugative -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. 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. In a systematic approach we synthesized a new series of fluorescent probes incorporating donor-acceptor (D-A) substituted 1,2,3-triazoles as conjugative pi -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 super(+) and K super(+) 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 super(+)/Na super(+)-select ive 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. 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. [PUBLICATION 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 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.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. |
| Author | Ast, Sandra Fischer, Tobias Müller, Holger Holdt, Hans-Jürgen Rurack, Knut Schwichtenberg, Mathias Mickler, Wulfhard |
| Author_xml | – sequence: 1 givenname: Sandra surname: Ast fullname: Ast, Sandra organization: Institut für Chemie, Anorganische Chemie, Universität Potsdam, Karl-Liebknecht Str. 24-25, 14467 Golm (Germany), Fax: (+49) 331-977-5055 – sequence: 2 givenname: Tobias surname: Fischer fullname: Fischer, Tobias organization: Fachbereich 1.9 Sensormaterialien, BAM Bundesanstalt für Materialforschung und -prüfung Richard-Willstätter Str. 11, 12489 Berlin (Germany) – sequence: 3 givenname: Holger surname: Müller fullname: Müller, Holger organization: Institut für Chemie, Anorganische Chemie, Universität Potsdam, Karl-Liebknecht Str. 24-25, 14467 Golm (Germany), Fax: (+49) 331-977-5055 – sequence: 4 givenname: Wulfhard surname: Mickler fullname: Mickler, Wulfhard organization: Institut für Chemie, Anorganische Chemie, Universität Potsdam, Karl-Liebknecht Str. 24-25, 14467 Golm (Germany), Fax: (+49) 331-977-5055 – sequence: 5 givenname: Mathias surname: Schwichtenberg fullname: Schwichtenberg, Mathias organization: Institut für Chemie, Anorganische Chemie, Universität Potsdam, Karl-Liebknecht Str. 24-25, 14467 Golm (Germany), Fax: (+49) 331-977-5055 – sequence: 6 givenname: Knut surname: Rurack fullname: Rurack, Knut email: knut.rurack@bam.de organization: Fachbereich 1.9 Sensormaterialien, BAM Bundesanstalt für Materialforschung und -prüfung Richard-Willstätter Str. 11, 12489 Berlin (Germany) – sequence: 7 givenname: Hans-Jürgen surname: Holdt fullname: Holdt, Hans-Jürgen email: holdt@uni-potsdam.de organization: Institut für Chemie, Anorganische Chemie, Universität Potsdam, Karl-Liebknecht Str. 24-25, 14467 Golm (Germany), Fax: (+49) 331-977-5055 |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/23319382$$D View this record in MEDLINE/PubMed |
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| Copyright | Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Keywords | 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 |
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| PublicationDate | February 25, 2013 |
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| PublicationSubtitle | A European Journal |
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| Publisher | WILEY-VCH Verlag WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
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| SubjectTerms | 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 |
| Title | Integration of the 1,2,3-Triazole "Click" Motif as a Potent Signalling Element in Metal Ion Responsive Fluorescent Probes |
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