Dual responsive chemosensors for anions : the combination of fluorescent PET (Photoinduced Electron Transfer) and colorimetric chemosensors in a single molecule

Gunnlaugsson, Thorfinnur, Kruger, Paul E., Lee, T. Clive, Parkesh, Raman, Pfeffer, Frederick M. and Hussey, Gillian M. 2003, Dual responsive chemosensors for anions : the combination of fluorescent PET (Photoinduced Electron Transfer) and colorimetric chemosensors in a single molecule, Tetrahedron letters, vol. 44, no. 35, pp. 6575-6578.

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Title Dual responsive chemosensors for anions : the combination of fluorescent PET (Photoinduced Electron Transfer) and colorimetric chemosensors in a single molecule
Author(s) Gunnlaugsson, Thorfinnur
Kruger, Paul E.
Lee, T. Clive
Parkesh, Raman
Pfeffer, Frederick M.
Hussey, Gillian M.
Journal name Tetrahedron letters
Volume number 44
Issue number 35
Start page 6575
End page 6578
Publisher Elsevier Ltd .
Place of publication Amsterdam, The Netherlands
Publication date 2003-08-25
ISSN 0040-4039
1873-3581
Summary The design and synthesis of two novel fluorescent PET anion sensors is described, based on the principle of ‘fluorophore-spacer-(anion)receptor’. The sensors 1 and 2 employ simple diaromatic thioureas as anion receptors, and the fluorophore is a naphthalimide moiety that absorbs in the visible part of the spectrum and emits in the green. Upon recognition of anions such as F and AcO in DMSO, the fluorescence emission of 1 and 2 was ‘switched off’, with no significant changes in the UV–vis spectra. This recognition shows a 1:1 binding between the receptor and the anions. In the case of F, further additions of the anion, gave rise to large changes in the UV–vis spectra, where the λmax at 455 nm was shifted to 550 nm. These changes are thought to be due to the deprotonation of the 4-amino moiety of the naphthalimide fluorophore. This was in fact found to be the case, using simple naphthalimide derivatives such as 6. Sensors 1 and 2 can thus display dual sensing action; where at low concentrations, the fluorescence emission is quenched, and at higher concentrations the absorption spectra are modulated.
Language eng
Field of Research 030302 Nanochemistry and Supramolecular Chemistry
HERDC Research category C1.1 Refereed article in a scholarly journal
Copyright notice ©2003, Elsevier Ltd.
Persistent URL http://hdl.handle.net/10536/DRO/DU:30028598

Document type: Journal Article
Collection: School of Life and Environmental Sciences
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