4-(1H-Imidazo[4,5-f][1,10]phenanthrolin-2-yl)benzaldehyde as a probe in pure solvents: Solvatochromism, electric dipole moment and pH influence

Abstract

The spectral properties of 4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)benzaldehyde (1) in eleven organic solvents of different polarity have been studied. In order to determine the contributions of specific and non-specific interactions between the considered compound and the solvents, the solvatochromic Lippert-Mataga, McRae, Bakhshiev methods have been applied. The compound demonstrates positive solvatochromism. The dipole moment of the excited state of 1 obtained using the Reichardt method is equal to 10.56/7.08 D for trans- and cis-conformers, respectively, and agrees well with the theoretically calculated value. The influence of the polarizability of 1 on changes in the dipole moments has been analyzed using the Bilot-Kawski method. The multiple linear regression analysis in the framework of the Kamlet-Abboud-Taft and Catalán models has highlighted that the main properties which determine the Stokes shift of 1 are the acidity and dipolarity of the solvent. The variation of pH by additions of acid or base to solution 1 leads to significant changes in absorption and fluorescence spectra, therefore, 1 can be of interest as a solvatochromic probe, being sensitive to acidic/base properties of the environment. It has also been found out that the anion form of 1 is present in the DMSO solution. An addition of N,N-dimethylcyclohexylamine intensifies the dissociation of the considered compound in the DMSO solution and suppresses the fluorescence at a large amine excess.