title: Water-soluble distyrylbenzenes: one core with two sensory responses--turn-on and ratiometric.
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 1b-3b in water reveal unexpected protonation sequences upon titration: compound 1b 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.
authors: Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
authors: Juan
authors: J
authors: Tolosa
authors: Jonathan J
authors: JJ
authors: Bryant
authors: Kyril M
authors: KM
authors: Solntsev
authors: Kerstin
authors: K
authors: Brödner
authors: Laren M
authors: LM
authors: Tolbert
authors: Uwe H F
authors: UH
authors: Bunz