Abstract
Schiff bases derived from 7-hydroxy-4-methyl-2-oxobenzo[h]chromene-8-carbaldehyde in solution exist as equilibrium mixtures of benzoid and quinoid tautomers. The fraction of the quinoid tautomer increases with rise in solvent polarity. The Schiff base containing a benzo-15-crown-5 fragment on the nitrogen atom was shown to be a new ambident chemosensor capable of selectively binding transition metal cations via reaction at the o-hydroxyaldehyde imine fragment and alkaline-earth metals via host-guest interaction with the crown ether moiety. This compound exhibits a pronounced sensor activity toward Mg2+ and Ba2+ ions and is a selective naked-eye fluorescent chemosensor for Cu2+ and Co2+ ions.
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Original Russian Text © L.G. Minyaeva, R.V. Tyurin, V.V. Mezheritskii, A.V. Tsukanov, E.N. Shepelenko, A.D. Dubonosov, V.A. Bren’, V.I. Minkin, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 12, pp. 1832–1836.
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Minyaeva, L.G., Tyurin, R.V., Mezheritskii, V.V. et al. Ambident chemosensors based on benzo[h]chromen-2-one. Russ J Org Chem 43, 1836–1841 (2007). https://doi.org/10.1134/S1070428007120172
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DOI: https://doi.org/10.1134/S1070428007120172