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 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.