Water-soluble distyrylbenzenes: one core with two sensory responses

• Verfasst von: Tolosa, Juan [VerfasserIn]
• Verfasst von: Bryant, Jonathan [VerfasserIn]
• Verfasst von: Solntsev, Kyril M. [VerfasserIn]
• Verfasst von: Brödner, Kerstin [VerfasserIn]
• Verfasst von: Tolbert, Laren M. [VerfasserIn]
• Verfasst von: Bunz, Uwe H. F. [VerfasserIn]
• Titel: Water-soluble distyrylbenzenes: one core with two sensory responses
• Titelzusatz: turn-on and ratiometric
• Verf.angabe: Juan Tolosa, Jonathan J. Bryant, Kyril M. Solntsev, Kerstin Brödner, Laren M. Tolbert, and Uwe H.F. Bunz
• E-Jahr: 2011
• Jahr: 02 November 2011
• Umfang: 6 S.
• Fussnoten: Gesehen am 10.11.2022
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2011
• Band/Heft Quelle: 17(2011), 49, Seite 13726-13731
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201102402
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: acidochromicity
• Sach-SW: amines
• Sach-SW: distyrylbenzene
• Sach-SW: fluorescence
• Sach-SW: photophysics
• K10plus-PPN: 1821597249

Abstract

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.