Estimation of Excited State Dipolemoments from Solvatochromic Shifts-Effect of pH.

Multicomponent, highly efficient, catalytic synthesis of some polysubstituted imidazole under solvent-free condition is reported. Characterization of polysubstituted imidazole have been carried out by X-ray diffraction (XRD) and spectral techniques. Electronic spectral studies reveal that their solvatochromic behavior depends not only on the polarity of the medium but also on the hydrogen bonding properties of the solvents. Specific hydrogen bonding interaction in polar solvents modulated the order of the two close lying lowest singlet states. The solvent effect on both the absorption and emission spectral results have been analyzed by multiple parametric regression analysis. Solvatochromic effects on the emission spectral position indicate the charge transfer (CT) character of the emitting singlet states both in a polar and a non polar environment. The fluorescence decays for the imidazole fit satisfactorily to a single exponential kinetics. The prototropic studies of N,N-dimethyl-4-(1,4,5-triphenyl-1H-imidazol-2-yl)naphthalen-1-amine (DTINA) reveal that two monocations [imidazole nitrogen protanated (MC1) and dimethylamino nitrogen protanated (MC2)] and a dication [both imidazole nitrogen and dimethylamino nitrogen protanated (DC)] are formed by protonation in both ground and excited states. These observations are in consistent with quantum chemical calculations.