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Water-soluble distyrylbenzenes: one core with two sensory responses: turn-on and ratiometric

The synthesis of four water-soluble distyrylbenzenes (compounds 1-4) is reported. Their acidochromicity in aqueous media was investigated. Blue shifts and increases in the quantum yields were observed as a general response. The pH-dependent photophysics of 1 b-3 b in water reveal unexpected protonat...

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Bibliographic Details
Main Authors: Tolosa, Juan (Author) , Bryant, Jonathan (Author) , Solntsev, Kyril M. (Author) , Brödner, Kerstin (Author) , Tolbert, Laren M. (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: 02 November 2011
In: Chemistry - a European journal
Year: 2011, Volume: 17, Issue: 49, Pages: 13726-13731
ISSN:1521-3765
DOI:10.1002/chem.201102402
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201102402
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201102402
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Author Notes:Juan Tolosa, Jonathan J. Bryant, Kyril M. Solntsev, Kerstin Brödner, Laren M. Tolbert, and Uwe H.F. Bunz
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Summary:The synthesis of four water-soluble distyrylbenzenes (compounds 1-4) is reported. Their acidochromicity in aqueous media was investigated. Blue shifts and increases in the quantum yields were observed as a general response. The pH-dependent photophysics of 1 b-3 b in water reveal unexpected protonation sequences upon titration: compound 1 b is green-yellow fluorescent at high pH (10) but becomes very weakly fluorescent between pH 5 and pH 3, whereas below pH 2 strong blue fluorescence is observed. This behavior can be explained in terms of the interplay in the protonation of aniline and of the carboxylate groups. In compound 4, a higher basicity of the amino group is observed and ratiometric fluorescence change takes place upon protonation or on reaction with zinc salts in water. Compound 4 can therefore act as a weak ratiometric zinc ligand in water, even though it has only a dimethylamino unit as a binding motif.
Item Description:Gesehen am 10.11.2022
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201102402

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