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


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Turan Y. N., Ermiş E.

6th Organic Chemistry Congress with International Participation, Eskişehir, Türkiye, 10 - 13 Eylül 2025, ss.103, (Özet Bildiri)

  • Yayın Türü: Bildiri / Özet Bildiri
  • Basıldığı Şehir: Eskişehir
  • Basıldığı Ülke: Türkiye
  • Sayfa Sayıları: ss.103
  • Atatürk Üniversitesi Adresli: Evet

Özet

Schiff base compounds are widely used as strong absorbent and colored chromophores in the design of chemosensors [1]. In recent years, a large number of Schiff base-based fluorescent probes have been developed for the detection of various toxic analytes and the imaging of different analytes in biological systems [2]. Schiff base-based chemosensors are easy and inexpensive to synthesize, and they can be used for the visual detection of different ions [3]. In addition, the effective and versatile functionalization of fluorescent BODIPY compounds at the 2,6-positions enables the preparation of BODIPY dyes with unique properties, which can serve as new building blocks for BODIPY-based sensor materials [4]. Therefore, in this study, a new Schiff base-substituted meso-4-(benzyloxy)phenyl BODIPY (3) compound, which can be a potential fluorescent sensor for the detection of various cations, was successfully synthesized via a condensation reaction between 2-formyl-meso-4-(benzyloxy)phenyl BODIPY (2) and 2-aminophenol (Figure 1) [5]. The characterization of BODIPY compounds (1–3) was performed using UV-Vis, FTIR, and 1H and 13C NMR spectroscopic techniques. In order to investigate the optimized molecular geometry, vibrational frequencies, UV-VIS spectroscopic parameters, HOMO-LUMO energy levels, 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 with experimental data, and good agreement was observed between them.