Highly Emissive Water-Soluble Polysulfurated Pyrene-Based Chromophores as Dual Mode Sensors of Metal Ions

Abstract

Pyrene-based materials have gained considerable attention as stimuli-responsive chemical sensors. We designed a polysulfurated arene system based on a tetra(phenylthio)pyrene core decorated with four carboxylic acid units. Three different regioisomers, ortho, meta and para were studied in organic and aqueous solution. These systems are soluble in water at pH≥8 due to the deprotonation of carboxylic acids. The addition of metal ions cannot only quench the fluorescence of the central pyrene core, but also control the formation of three-dimensional nanoscopic objects in a dual mode function. Several divalent metal ions were tested and compared. Addition of ethylenediaminetetraacetic acid (EDTA) disassembles the non-emissive supramolecular system and restores the initial fluorescence of the pyrene core.

Keywords: luminescence; metal ions; pyrenes; sensors; supramolecular chemistry.