Bipyridyl– and pyridylquinolyl–phenothiazine structures as potential photoactive ligands: Syntheses and complexation to palladium
| Autor: | Jonathan Mendy, Alexis Tabey, Eric Fouquet, Philippe Hermange |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Absorption spectroscopy
010405 organic chemistry Organic Chemistry Cyclohexane conformation Organometallic catalysis chemistry.chemical_element 010402 general chemistry Photochemistry 01 natural sciences Biochemistry 0104 chemical sciences chemistry.chemical_compound Bipyridine chemistry Phenothiazine Drug Discovery Polymer chemistry Proton NMR Moiety Palladium |
| Zdroj: | Tetrahedron Letters. 58:3096-3100 |
| ISSN: | 0040-4039 |
| Popis: | Three new bipyridyl– and pyridylquinolyl–phenothiazine structures were synthesized through Pd-catalyzed C–N couplings between phenothiazine and the corresponding bromo-heteroaryls. For the 2-(N-phenothiazine)-bipyridine, boat conformation was determined for the phenothiazine moiety by X-ray diffraction analysis. Single well-defined palladium acetate complexes were observed by 1H NMR analysis with the 4-(N-phenothiazine)-bipyridine and the pyridyl-5-(N-phenothiazine)-quinoline. Compared to the naked ligands, the UV–visible absorption spectra showed, in these cases, significantly red shifted λmax upon coordination. Preliminary modeling experiments with the free and the coordinated 4-(N-phenothiazine)-bipyridine suggested for both the occurrence of electronic transfers from the phenothiazine to the bipyridine. Potentially enabling the tuning of the electron density of the coordinating moiety upon near-UV irradiation, this bipyridyl–phenothiazine structure could be the origin of a novel class of photo-active ligands for applications in organometallic catalysis. |
| Databáze: | OpenAIRE |
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