Solvent Effect on the Photophysical Properties of Terpyridine Incorporating Pyrene Moiety: Estimation of Dipole Moments by Solvatochromic Shift Methods

The absorption and fluorescence emission spectra of terpyridine incorporating pyrene moiety (Tpy-pyr) have been recorded in extensive variety of solvents having different polarities. The effect of the solvent on the spectral characteristics are examined. It is shown that Tpy-pyr exhibit positive solvatochromism, large Stokes shift values in polar solvents, and fluorescence in the long wavelength region of the visible range. A linear increasing trend with Stokes shift indicates the presence of Tpy-pyr - solvent interaction. The acquired results could be attributed to the formation of excited states with intramolecular charge transfer. The fluorescence quantum yield was drastically reduced in polar protic solvents and the formation of the twisted states with charge transfer was proposed. Both ground and excited state dipole moments (µg and µe) were determined experimentally by Lippert–Mataga, Reichardt, Bilot-Kawski, Bakhshiev and Kawski-Chamma-Viallet solvatochromic methods analyzed on the base of the microscopic solvent polarity functions. The µg and µe dipole moment of Tpy-pyr estimated from density functional theory (DFT) and those determined experimentally from solvatochromic methods are compared and the results are discussed.