Sensor activity and logic behavior of dihydroxyphenyl hydrazone derivative as a chemosensor for Cu2+ determination in alkaline aqueous solutions

• A novel highly water-soluble in alkaline window hydrazone derivative is synthesized.
• Compound is designed as an “off–on–off” molecular pH probe.
• Probe manifests selective signaling response to Cu2+ in alkaline aqueous medium.
• Logic functions disabled XNOR and disabled IMPLICATION are achieved.
• Two output combinatorial logic circuit with three chemical inputs is demonstrated.
• Probe is able to work as a magnitude digital comparator with disable capability.

The synthesis, sensor activity and logic behavior of a novel highly water-soluble under alkaline conditions dihydroxyphenyl hydrazone derivative is reported. The changes in the photophysical properties of the compound as a function of pH were investigated. Novel hydrazone manifests “off–on–off” fluorescence response toward pH in alkaline window due to the reversible transformation of the monophenolate ion into a keto-hydrazine dianion and deprotonation of the trifluoroacetamide moiety in strong alkaline media. The synthesized compound shows excellent selective signaling properties toward Cu2+ ions over the representative metal ions. Due to the remarkable absorption and fluorescence changes as a function of pH and in the presence of Cu2+ ions novel compound is able to act as a two output combinatorial logic circuit with three chemical inputs. It executes disabled XNOR and IMPLICATION gates, therefore is capable of working as a magnitude digital comparator with disable capability.