Experimental and theoretical study on structure and spectroscopic properties of 2‐bromo‐3‐N‐(N′,N′‐dimethylformamidino) benzanthrone

Abstract

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.

Comparison of the Benzanthrone Luminophores: They Are Not Equal for Rapid Examination of Parafasciolopsis fasciolaemorpha (Trematoda: Digenea)

“…The molecular weight is 379.26 g mol −1 . The dye AM323 was obtained from 3-amino-2-bromobenzanthrone accordingly to the described procedure [40].…”

Quantum chemical computations, fluorescence spectral features and molecular docking of two biologically active heterocyclic class of compounds

“…Also, correlations are found between the theories of second order perturbation and that of quantum mechanical Onsager's reaction field [6][7][8][9][10][11][12][13]. In structural discovery, coumarin compounds are found to have an extensive significance [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31]. For the design of new pharmaceutical compounds, the information on local reactivity descriptors based on charge density and molecular reactivity is provided by density functional theory (DFT) .…”

Quantum chemical computations and photophysical spectral features studies of two coumarin compounds

“…Quantum mechanical Onsager's reaction field theories and second order perturbation theory have been correlated . Coumarin compounds have high potential application and extensive significance in structural discovery . Density functional theory (DFT) provides valuable information on molecular reactivity and charge density‐based local reactivity descriptors, which play a significant role in the design of new pharmaceutical compounds .…”