A new use for an old molecule: N-phenyl-2-(2-hydroxynaphthalen-1-ylmethylene)hydrazinecarbothioamide as a ratiometric `Off-On' fluorescent probe for iron

Maria Jose Casanueva Marenco, Colin Fowley, Barry W. Hyland, Graham R. C. Hamilton, Dolores Galindo-Riano, John F. Callan

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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 mu M range. The binding stoichiometry was confirmed as 1:1 (host/guest) with the binding constant (log beta) calculated as 4.56. (C) 2011 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)670-673
JournalTetrahedron Letters
Issue number6
Publication statusPublished - Feb 2012



  • Fluorescence
  • Sensor
  • Iron(III)
  • Ratiometric

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