Experimental and theoretical study on solvent and substituent effect in 3-(4-substituted)phenylamino)isobenzofuran-1(3H)-ones

Nevena Prlainović, Milica Rančić, Ivana Stoiljković, Jasmina Nikolic, Saša Drmanić, Ismail Ajaj, Aleksandar Marinković


The substituent and solvent effect on solvatochromism in3-((4-substituted)phenylamino)isobenzofuran-1(3H)-ones were studied using experimental and theoretical methodology. The effect of specific and non-specific solvent–solute interactions on the UV-Vis absorption maxima shifts were evaluated by using the Kamlet-Taft and Catalán solvent parameter sets. The experimental results were studied by DFT and TD-DFT methods. The HOMO/LUMO energies (EHOMO/ELUMO) and energy gap (Egap) values, as well as the mechanism of electronic excitations and the changes in the electron density distribution in both ground and excited states of the investigated molecules were studied by the calculation in the gas phase. The electronic excitations were calculated by TD-DFT method in solvent methanol. It was found that both substituents and solvents influence the degree of π-electron conjugation of the synthesized molecules and affect the intramolecular charge transfer character. 


phthalides; solvatochromism; substituent effect; LSER; quantum chemical calculation.

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DOI: http://dx.doi.org/10.2298/JSC170408003P


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