SYNTHESIS AND SPECTRAL PROPERTIES OF BODIPY LUMINOPHORE WITH EXTENDED π-ELECTRONIC SYSTEM

Abstract

We report the synthesis, purification and identification of a new derived class of BODIPY - of naphtho-fused BODIPY analogue, 8-(3,5-dimethylphenyl)-4,4-difluoro-4-bora-3a,4a-diaza-dinapht-[1,2b][1,2c]-s-indacene. A detailed method for obtaining the compound was given. The structure was confirmed by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectrometry. Electronic absorption and fluorescence spectra were obtained in solvents of different nature. The effect of solvent nature on the positions of absorption and fluorescence peaks and Stokes shift has been studied. It has been shown that the nature of the solvent has a significant effect on the fluorescence intensity and does not significantly effect the position of the absorption peaks. The photophysical characteristics of the compound were compared with known alkylated analogues. It is shown that the expansion of the electronic system leads to a bathochromic shift in the electronic absorption and fluorescence spectra. Quantum-chemical calculations of the electronic absorption and fluorescence spectra were carried out using the TDDFT (time dependent density functional theory) method. The influence of the extended π-electron system on the position and character of the absorption and fluorescence spectra was studied. It is shown that the presence of naphthalene fragments conjugated with the BODIPY core leads to a bathochromic shift of the absorption and fluorescence bands, as well as a partial change in the character of the spectra. The energy levels and electronic structure of the FMOs with the TDDFT method were calculated. The calculated data are in good agreement with the results obtained by experimental methods. The results obtained, in turn, are consistent with the results obtained earlier by our scientific group. Compounds that possess such properties are especially important and could be used in such practical applications as photovoltaics, photodynamic therapy of oncological diseases and as agents for visualization of biomolecules.