Synthesis and photophysical studies on a new fluorescent phenothiazine-based derivative

A new typical phenothiazine compound functionalized with thienyl-indandione derivative (PTZTID) was synthesized and characterized using spectral analysis (ultraviolet-visible (UV-vis) light, infrared (IR), H-1 nuclear magnetic resonance (NMR) and C-13 NMR tools). The UV-vis absorption spectra of the PTZTID solution in 1,4-dioxane showed two absorption bands attributed to localized aromatic pi-pi* transitions of conjugated aromatic moieties and intramolecular charge transfer with the characteristics of a pi-pi* transition. The fluorescence spectra exhibited a maximum emission wavelength at 580 nm. The effect of concentration on photophysical properties took the form of a minor hypsochromic shift, which was attributed to some extent to the occurrence of H-type aggregation of the PTZTID derivative. Binary solvent effects on the spectroscopic behaviour of PTZTID were measured at different H2O/1,4-dioxane ratios. Similarly, when increasing the water content, a hypsochromic shift was observed that resulted from H-type aggregation. Furthermore, geometry and electronic configurations of PTZTID were studied at density functional theory /B3LYP level and indicated that the compound had a nonplanar (butterfly structure).