Quinazolinone derivative: Model compound for determination of dipole moment, solvatochromism and metal ion sensing.

A dihydroquinazolinone derivative 2-(2,4-Dimethoxy-phenyl)-2,3-dihydro-1H-quinazolin-4-one ( 1 ) was synthesized and characterized by 1 H NMR, 13 C NMR and FT-IR and its spectral, photophysical, intramolecular charge transfer characteristics were studied by absorption and emission spectroscopy. The compound exhibits significant changes in their photophysical properties depending on the solvent polarity. The observed bathochromic emission band and difference in Stokes shift on changing the polarity of the solvents clearly demonstrate the highly polar character of the excited state, which is also supported by the enhancement of dipole moment of the molecule upon photoexcitation. Solvatochromic shift methods based on Lippert–Mataga, Bakhshiev-Kawski and Reichardt's correlations were applied to calculate the ground, excited and change in dipole moments. The effect of solute–solvent interactions on compound 1 was studied using multi-parameter solvent polarity scales proposed by Kamlet–Taft and Catalan. The interactions of various metal ions on compound 1 were also studied using steady state fluorescence measurements. The emission profile reveals that it acts as on-off type fluorescent chemosensor for selective and sensitive detection of Hg 2 + ions. Complexation stoichiometry and mechanism of quenching were determined from Benesi–Hildebrand and Stern-Volmer plot. [ABSTRACT FROM AUTHOR]