Synthesis, structure, and luminescent properties of 2-[2-(9-anthryl)vinyl]quinolines
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Previously unknown 2-[2-(9-anthryl)vinyl]quinolin-8-ol and 2-[2-(9-anthryl)vinyl]-8-methoxyquinoline were synthesized by condensation of 8-hydroxy(methoxy)-2-methylquinoline with 9-anthraldehyde in acetic anhydride, as well as by the Wittig reaction. The product structure was determined on the basis of their 1H NMR, IR, UV, and mass spectra and quantum-chemical calculations. 2-[2-(9-Anthryl)vinyl]-8-methoxyquinoline showed luminescence with a quantum yield φ of 0.25, which was considerably higher than that of its 8-hydroxy analog (φ = 0.067).
KeywordsQuinoline Lower Unoccupied Molecular Orbit Trans Isomer Ethenyl Quinoline Ring
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