SYNTHESIS, CHARACTERIZATIONS AND DFT CALCULATIONS OF A NOVEL SCHIFF BASE-SUBSTITUED meso-4-(BENZYLOXY)PHENYL BODIPY COMPOUND

<p class="Default" style="text-align:justify;line-height:150%"><span style="font-size:11.0pt;line-height:150%">Schiff base compounds are widely usedas strong absorbent and colored chromophores in the design of chemosensors <b>[1]</b>. In recent years, a large number ofSchiff base-based fluorescent probes have been developed for the detection ofvarious toxic analytes and the imaging of different analytes in biologicalsystems <b>[2]</b>. Schiff base-basedchemosensors are easy and inexpensive to synthesize, and they can be used forthe visual detection of different ions <b>[3]</b>.In addition, the effective and versatile functionalization of fluorescentBODIPY compounds at the 2,6-positions enables the preparation of BODIPY dyes withunique properties, which can serve as new building blocks for BODIPY-basedsensor materials <b>[4]</b>. Therefore, inthis study, a new Schiff base-substituted <i>meso</i>-4-(benzyloxy)phenylBODIPY <b>(3)</b> compound, which can be apotential fluorescent sensor for the detection of various cations, wassuccessfully synthesized via a condensation reaction between 2-formyl-<i>meso</i>-4-(benzyloxy)phenyl BODIPY <b>(2)</b> and 2-aminophenol <b>(Figure 1) [5]</b>. The characterization ofBODIPY compounds <b>(1–3)</b> was performedusing UV-Vis, FTIR, and ¹H and ¹³C NMR spectroscopictechniques. In order to investigate the optimized molecular geometry,vibrational frequencies, UV-VIS spectroscopic parameters, HOMO-LUMO energylevels, atomic charge distributions, and molecular electrostatic potential (MEP)map of the BODIPY compound, Density Functional Theory (DFT/B3LYP/6-311G(d,p))calculations were carried out. Theoretical results were compared withexperimental data, and good agreement was observed between them.<o:p></o:p></span>