A new use for an old molecule: N-phenyl-2-(2-hydroxynaphthalen-1-ylmethylene)hydrazinecarbothioamide as a ratiometric ‘Off–On’ fluorescent probe for iron
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Author/sCasanueva Marenco, María José; Fowley, Colin; W. Hyland, Barry; R.C. Hamilton, Graham; Galindo Riaño, María Dolores; F. Callan, John
SourceTetrahedron Letters 53 (2012) 670–673
N-Phenyl-2-(2-hydroxynaphthalen-1-ylmethylene)hydrazinecarbothioamide has been investigated as a fluorescent sensor for the determination of Fe(III) in aqueous solutions. The probe was prepared by the facile Schiff base condensation of 2-hydroxy-1-napthaldehyde with N-phenylhydrazinecarbothioamide. The sensor displayed good selectivity for Fe(III) when tested against a range of biologically and environmentally important cations. A concentration dependent increase in the emission of two fluorescent bands at 425 and 495 nm was observed upon increasing Fe(III) addition resulting in a linear ratiometric response in the 17–37 lM range. The binding stoichiometry was confirmed as 1:1 (host/guest) with the binding constant (logb) calculated as 4.56.