Synthesis, characterization and theoretical calculations of novel substituted bodipy compounds

In this dissertation, novel functionalized BODIPYs at meso-, 2- and/or 2,6-positions have been synthesized with moderate yields. In order to extend the conjugation of the starting BODIPYs 2a-c and modify their structural and electronic properties, significant functional groups such as Br atom, thienyl moiety, formyl group and aryl imin have been introduced into the 2 and/or 2,6 positions of the BODIPY core via several reactions. All the synthesized BODIPYs have been characterized by using UV-Vis, fluorescence, FTIR, 1H, 13C and 19F NMR spectroscopic techniques. The absorption and fluorescence spectroscopy were used to examine the electronic behaviors of all the BODIPYs. The red shift was observed in the absorption (25-46 nm) wavelengths of bromo-substituted BODIPYs obtained by bromination of α,β-unsubstituted-meso-(thienyl) BODIPYs 2a-c. Functionalization with thienyl moiety at 2- or 2,6-positions on BODIPY skeleton as electron donor caused the redshifts in the absorption (46-100 nm) and in the emission (27-78 nm) in comparison to α,β-unsubstituted BODIPYs 2a-c. Schiff base BODIPYs 11-13(a-j) exhibited redshift in the absorption depending on the substituents in the aromatic phenyl ring. The theoretical characterization of BODIPY 2a and its derivatives was accomplished using the DFT/B3LYP/6-311G(2d,p) and TD-DFT calculations. The energies of HOMO-LUMO, the atomic charges and the MEP surface for these BODIPYs were investigated using the DFT/B3LYP/6-311G(2d,p) method. The obtained theoretical results were compared with the experimental data. In addition, the antibacterial activities of BODIPY 2a and its derivatives have been investigated against Bacillus cereus, Micrococcus luteus, Staphylococcus aureus, Escherichia coli and Listeria monocytogenes.