Selective sensing of cyanide ions: impact of molecular design and assembly on the response of π-conjugated acylhydrazone compounds

Abstract

This study investigates the sensing properties of two distinct compounds, denoted as 1 and 2, featuring acylhydrazone units. Spectroscopic analyses reveal the disruption of the supramolecular assembly upon binding with cyanide ions, consequently due to the hydrogen bonding interaction with acylhydrazone units. This leads to a ratiometric, color-changing response of both the compounds specifically towards cyanide ions. The investigation sheds light on the reversible nature of the cyanide-probe interaction and highlights the potential for reusability in cyanide ion detection. Moreover, compound 1, distinguished by its long alkyl chains, displays a superior response to CN⁻ ions (∼4-fold larger signal), in contrast to compound 2. However, interference was observed from other basic anions, such as F⁻ and AcO⁻. The research suggests the dominating role of supramolecular assembly, intermolecular interaction, and local hydrophobic environment around the binding sites on the analytical performance of the probe molecules. The findings underscore the significance of structural design and molecular assembly in dictating the selectivity and sensitivity of compounds, offering valuable insights for the development of efficient sensor systems in diverse real-world applications.