Synthesis of Hydrazone Based Ion Sensor and Photophysical Characterization

Hydrazone compounds are susceptible to nucleophilic attacks of anions such as fluoride or cyanide due to their tendency toward deprotonation of hydrogen bonded to nitrogen atom in the structure and found applications as ion sensors. In this work, from the condensation reaction of 4-hydroxybenzaldehyde and 2,4-dinitrophenylhydrazine, phenolic hydrazone compound was obtained and the following substitution reaction with 4-nitrobenzenesulfonyl chloride was studied to synthesize a new hydrazone compound with elongated conjugation. Structures of the synthesized compounds were accomplished with 1H NMR, 13C NMR an UV-Vis absorption spectroscopic techniques. According to the spectroscopic data, absorption maximum of the new hydrazone compound was found to shift bathochromically with ca. 120 nm in the presence of nucleophilic fluoride, cyanide, acetate and hydroxide anions.