The goal of present research is a theoretical and experimental investigation of geometrical structure, electronic properties, absorption and fluorescence spectra prediction for 2-bromo-3-N-(N',N'-dimethylformamidino)benzanthrone. As a result of conformational analysis, two rotamers have been found with a rotational barrier of 5.45 kcal/mol. Absorption and fluorescence spectra maxima in the solvent (ethanol) have been calculated using the concepts of the Jablonsky diagram. The obtained values of the absorption and fluorescence maxima (437 and 679 nm, respectively) correspond to the experimental values (447 and 659 nm). The abnormally large Stokes shift is associated with the redistribution of electron density, as well as flattening of the structure of the molecule in the excited state. According to the frontal molecular orbital analysis data, the peak in the long-wave part of the absorption spectra is created by an electron transition from the highest occupied molecular orbital (HOMO) to the lowest occupied molecular orbital (LUMO) (π→π*). Substitute group does not participate in the formation of absorption and fluorescence spectra.
Keywords: PM6 and DFT calculations; X-ray crystallography; absorption; benzanthrone; fluorescence.
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