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XPS and quantum chemical analysis of 4Me-BODIPY derivatives

2023; Royal Society of Chemistry; Volume: 25; Issue: 6 Linguagem: Inglês

10.1039/d2cp04541a

1463-9084

Sergey A. Tikhonov, Andrey E. Sidorin, Alexander A. Ksenofontov, D.Yu. Kosyanov, Ilya S. Samoilov, A. D. Skitnevskaya, А. Б. Трофимов, Е. В. Антина, М. Б. Березин, V. I. Vovna,

Porphyrin and Phthalocyanine Chemistry

The results of a X-ray photoelectron spectroscopy (XPS) and steady-state absorption spectroscopy study of the electronic structure, and cationic and excited states of a series of 1,3,5,7-tetramethyl-substituted BODIPYs (4Me,2R-BODIPYs) are presented. The experimental data were interpreted using high-level ab initio quantum chemical computations, including the algebraic diagrammatic construction method for the polarization propagator of the second order (ADC(2)), the outer-valence Green's function (OVGF) method, the density functional (DFT) approach, and the time-dependent DFT (TD-DFT) approach. Substitution effects on the XPS and absorption spectra were determined for 2,6-positions of 4Me,2R-BODIPY pyrrole nuclei (R = H, Br, Bu, benzyl). A very satisfactory performance of the DFT Koopmans theorem analogue was demonstrated with respect to the energy intervals between the electronic levels of 4Me,2R-BODIPY above 13 eV (BHHLYP functional) and the values of the HOMO-LUMO energy gap (ωB97X functional).