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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| Hauptverfasser: | , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
02 November 2011
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| In: |
Chemistry - a European journal
Year: 2011, Jahrgang: 17, Heft: 49, Pages: 13726-13731 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201102402 |
| Online-Zugang: | 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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| Verfasserangaben: | Juan Tolosa, Jonathan J. Bryant, Kyril M. Solntsev, Kerstin Brödner, Laren M. Tolbert, and Uwe H.F. Bunz |
MARC
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| 520 | |a 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. | ||
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| 650 | 4 | |a distyrylbenzene | |
| 650 | 4 | |a fluorescence | |
| 650 | 4 | |a photophysics | |
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