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Updated: Dec 30, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Synthesis, modelling, and solvatochromic properties of a phenothiazine derivative
1Chemistry Department, Faculty of Science, King Khalid University, P.O. Box 9004, Abha, Saudi Arabia.
Abstract:
A new A-π-D-π-A phenothiazine derivative, 2,2'-((10-octyl-10H-phenothiazine-3,7-diyl)bis (ethene-2,1-diyl))bis(1-ethyl-3,3-dimethyl-3H-indol-1-ium)iodide (PTZ-BEI) was prepared and fully characterized using infra-red (IR), 1 H nuclear magnetic resonance (NMR), 13 C NMR, ultraviolet-visible light and mass spectra. Electronic spectra of PTZ-BEI solutions in solvents with different polarities displayed absorption bands (λmax ) related to intramolecular charge transfer. In addition, the emission spectra of PTZ-BEI solutions were strongly solvent dependent for both wavelength and intensity. Stokes' shift ( increased with increasing solvent polarity up to 4105 cm-1 in the most polar solvent, dimethylformamide. The linear solvation-energy relationship was utilized to investigate solvent dependency of the Stokes' shifts. Relative quantum yield (φ) of PTZ-BEI was calculated. Finally, density functional theory was employed at the B3LYP level for geometrical optimization and simulation of electron spectra for the PTZ derivative in gaseous and solvated states to explore the solvent effect.
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