A reaction based carbazole–indolium conjugate probe for the selective detection of environmentally toxic ions

Abstract

A nucleophilic addition based chemodosimeter was designed and synthesized with a carbazole donor and an indole acceptor. The addition of a cyanide ion to an electron-deficient indole moiety disrupts the acceptor–donor relationship, resulting in noticeable color shifts and spectrum differences in both the absorption and emission profiles. The design has a D–π–A molecular arrangement. Selectivity was investigated in 90% aqueous DMSO solution of probe CI with various anions such as SCN⁻, PF₆⁻, NO₃⁻, N₃⁻, I⁻, HSO₄⁻, CN⁻, H₂PO₄⁻, F⁻, HS⁻, ClO₄⁻, Cl⁻, Br⁻, and AcO⁻. An intermolecular charge transfer (ICT) band at 506 nm in the UV-visible spectra vanished and the intensity of emission was quenched at 624 nm upon the addition of CN⁻ ions. These outcomes demonstrate the effective nucleophilic addition of cyanide ions to the electron-deficient indole moiety of the probe, resulting in the formation of a new adduct in which the ICT transition is interrupted when π conjugation is blocked. The Job plot, ¹H NMR spectroscopy, and HRMS analysis confirmed the formation of a new product. An outstanding response was shown by paper test strips made using probe molecules for the easy detection of cyanide ions in aqueous solutions. Besides, the probe selectively senses cyanide ions in different water samples.