Synthesis of New Schiff Bases Including of Terephthalohydrazide and Sensor Application

Abstract

Schiff bases are compounds that are formed by the reaction of aldehydes or ketones with primary amines, usually in alcoholic solution and in a neutral environment, and contain carbon-nitrogen (C=N) double bonds, called the azomethine or imine group, in their structure because of the condensation reaction. In recent years, Schiff Base-based molecular sensors have been one of the most emphasized topics by scientists. In this study, the 3'-formyl-4'-hydroxy-[1,1'-biphenyl]-4-carbonitrile was obtained as literature information (Alici & Erdemir, 2015). Then, for the target compound, which is Schiff base derivative, was obtained from the condensation reaction of the 3'-formyl-4'-hydroxy-[1,1'-biphenyl]-4-carbonitrile with terephthalohydrazide. Chemical structure of synthesized Schiff base compound was confirmed as using various spectroscopic techniques (1H-NMR and 13C-NMR). Then, the interactions of the synthesized Schiff base compound with metals (Fe3+, Ag+ , Ca2+, Cr3+, Li+ , Sr2+, Ni2+, Ba2+, Pb2+, Mn2+, Cd2+, Hg2+, Co2+, Cu2+, Cs+ , Na+ , Mg2+, Fe2+ , Zn2+, Al3+) under convenient conditions were investigated using fluorescence spectrophotometry. In the fluorimetric investigations, primarily, the selectivity study was carried out. The free sensor target compound at 489 nm did not produce any significant emission intensity with excitation at 360 nm. The each of the cations (10.0 equiv) were separately added to target compound, only Al3+ caused to a single band at 489 nm with a notable emission enhancement. As a result of the measurements, it was determined that the target compound had fluorimetric selectivity against only Al3+ metal within all metals (Fe3+, Ag+ , Ca2+, Cr3+, Li+ , Sr2+, Ni2+, Ba2+ , Pb2+, Mn2+, Cd2+, Hg2+, Co2+, Cu2+, Cs+ , Na+ , Mg2+, Fe2+, Zn2+).

Keywords

• Hydrazide
• Fluorescence
• Al3+
• Schiff base.

References

1. Alici, O., & Hameed, A. A. (2024). Synthesis of new schiff bases including of terephthalohydrazide and sensor application. The Eurasia Proceedings of Science, Technology, Engineering & Mathematics (EPSTEM), 29, 113- 119.