Synthesis, Crystal Structure and Substituent Controlled Photoluminescence and Chemosensing Properties of a Series of 2,2′‐(Arylenedivinylene)bis‐8‐hydroxyquinolines

Abstract

AbstractA series of new π‐conjugated oligomeric compounds, 2,2′‐(arylenedivinylene)bis‐8‐hydroxyquinolines, having two vinylene‐8‐hydroxyquinoline moieties structured around a phenol ring, have been synthesized by the reaction of 8‐hydroxyquinaldine with aromatic dialdehydes. Crystal structure of one of the compounds has been described, which shows a twisted molecular geometry and interesting supramolecular interactions leading to a 2‐D sheet‐like structure in the crystal lattice. The photo‐luminescence properties analyses revealed that the fluorescence emission wavelengths of these compounds vary in the range 480–638 nm depending on the electronic effects of the substituents on the central phenol ring. These compounds were found to act as selective and sensitive fluorescence turn‐off chemosensors for Co2+ ions and the detection limits exhibited by these chemosensors varied in the range 15.00‐23.09 nM. Analytical application of these compounds for sensing cobalt from tap water in nanomolar levels is demonstrated. Preliminary investigations conducted using HeLa cells revealed their potential for sensing cobalt in biological systems.