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Synthesis and Luminescence and Ionochromic Properties of 9-Hydroxy-1-methyl-3-oxo-3H-benzo[f]chromene8-carbaldehyde Imines and Hydrazones

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Formylation of 9-hydroxy-1-methyl-3H-benzo[f]chromen-3-one with hexamethylenetetramine in acetic acid afforded 9-hydroxy-1-methyl-3-oxo-3H-benzo[f]chromene-8-carbaldehyde which was converted to the corresponding aldehyde imines and aroylhydrazones. According to the 1H NMR and UV spectral data, 9-hydroxy-1-methyl-3-oxo-3H-benzo[f]chromene-8-carbaldehyde… Click to show full abstract

Formylation of 9-hydroxy-1-methyl-3H-benzo[f]chromen-3-one with hexamethylenetetramine in acetic acid afforded 9-hydroxy-1-methyl-3-oxo-3H-benzo[f]chromene-8-carbaldehyde which was converted to the corresponding aldehyde imines and aroylhydrazones. According to the 1H NMR and UV spectral data, 9-hydroxy-1-methyl-3-oxo-3H-benzo[f]chromene-8-carbaldehyde imines in solution exist as ketone tautomers, whereas its aroylhydrazones have enol structure. 9-Hydroxy-1-methyl-3-oxo-3H-benzo[f]chromene-8-carbaldehyde aroylhydrazones are multifunctional ionochromic compounds capable of forming colored complexes with d metal cations, as well as with fluoride, cyanide, and acetate anions. The complexation leads to switching of the absorption and fluorescence properties of the initial compounds. Metal cations cause naked-eye visible change of the solution color from colorless to bright orange and fluorescence quenching, whereas in the presence of anions the color changes to red in combination with a red shift and increase in the emission intensity.

Keywords: hydroxy methyl; oxo benzo; methyl oxo; methyl

Journal Title: Russian Journal of General Chemistry
Year Published: 2020

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