Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 36, Pages 9984-9998Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201100592
Keywords
chromophores; cyclic voltammetry; dyes/pigments; electro-optical absorption spectroscopy; fluorescence; heterocycles
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Funding
- Fonds der Chemischen Industrie
- Volkswagen Foundation
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Phenothiazinyl merocyanine dyes with variable substitution patterns on the peripheral benzene ring were synthesized in good yields by Knoevenagel condensation of the corresponding phenothiazinyl aldehydes and N-methylrhodanine or indan-1,3-dione. The electronic properties were investigated by cyclic voltammetry, absorption, electro-optical absorption, and emission spectroscopy. All these merocyanines reveal reversible redox behavior that stems from the phenothiazinyl-centered oxidation to give stable radical cations. The redox potentials strongly correlate with Hammett sigma(p) parameters. All merocyanines reveal large Stokes shifts. They also display a pronounced emissive solvatochromism, which is caused by large dipole moment changes upon excitation from the ground to the excited state. These findings are supported by solvatochromism studies and time-dependent DFT computations.
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