Pyrene Substituted Phthalonitrile Derivative As a Fluorescent Sensor For Detection of Fe Ions in Solutions.

In this current study, the novel bis[4,5-(pyrene-2-yl)-3,6-(hexyloxy)] phthalonitrile (SPN) fluorophore has been successfully synthesized. Structural characterization of this novel compound was performed by different spectroscopic methods such as FT-IR, MALDI-TOF, H-NMR, C-NMR and elemental analyses as well. In addition, the photophysical properties were determined using UV-vis absorption, steady-state fluorescence, time-resolved fluorescence spectroscopic methods and quantum chemical calculations. The metal sensing behavior of the SPN was determined in the presence of various metals (Li, Na, K, Mg, Ca, Ba, Mn, Fe, Cr, Co, Ni, Ag, Cd, Al, Hg and Zn) using fluorescence spectroscopy. The novel pyrene based phthalonitrile (SPN) showed high sensitivity and selectivity towards Fe ion over other examined metal ions. In order to perform the determination of Fe ion in environmental samples, experimental conditions such as selectivity, stability, precision, sensitivity, accuracy and recovery were optimized. Also, the complex stoichiometry of the novel pyrene based phthalonitrile (SPN) and Fe ions was determined by a Job's plot. The compound was also studied via density functional theory calculations revealing the interaction mechanism of the molecule with Fe ions.