Fluorescence response of TICT-active aminostilbenes to copper(II) ions: redox reaction vs ion recognition

Fluorescence response of TICT-active aminostilbenes to copper(II) ions: redox reaction vs ion... Cu(II)-selective fluorescence enhancement (1, 2, and 4) or fluorescence quenching (3) was observed for aminostilbenes 1–4 in acetonitrile. The fluorescence responses result from efficient Cu(II)-mediated oxidation of 1–4 that forms new fluorescent species rather than from any specific noncovalent interactions. Evidence of redox reactions includes irreversible Cu(II) titration spectra, spectroscopic observation of the radical cations, and isolation of oxidized aminostilbene dimers. These results provide a new method for synthesis of tetrasubstituted tetrahydrofurans and suggest that aminostilbenes with twisted intramolecular charge-transfer activity are potential fluorescence-enhanced Cu(II) chemodosimeters. The role of Cu(II)-mediated redox reactions should be always taken into account in mechanisms for sensing of arylamine-based Cu(II)-selective fluoroionophores. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Fluorescence response of TICT-active aminostilbenes to copper(II) ions: redox reaction vs ion recognition

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Publisher
Springer Netherlands
Copyright
Copyright © 2012 by Springer Science+Business Media B.V.
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-012-0627-5
Publisher site
See Article on Publisher Site

Abstract

Cu(II)-selective fluorescence enhancement (1, 2, and 4) or fluorescence quenching (3) was observed for aminostilbenes 1–4 in acetonitrile. The fluorescence responses result from efficient Cu(II)-mediated oxidation of 1–4 that forms new fluorescent species rather than from any specific noncovalent interactions. Evidence of redox reactions includes irreversible Cu(II) titration spectra, spectroscopic observation of the radical cations, and isolation of oxidized aminostilbene dimers. These results provide a new method for synthesis of tetrasubstituted tetrahydrofurans and suggest that aminostilbenes with twisted intramolecular charge-transfer activity are potential fluorescence-enhanced Cu(II) chemodosimeters. The role of Cu(II)-mediated redox reactions should be always taken into account in mechanisms for sensing of arylamine-based Cu(II)-selective fluoroionophores.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Jun 14, 2012

References

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