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

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

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.
LanguageEnglish
Pages670-673
JournalTetrahedron Letters
Volume53
Issue number6
DOIs
Publication statusPublished - Feb 2012

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Fluorescent Dyes
Iron
Molecules
Schiff Bases
Sensors
Stoichiometry
Cations
Condensation

Keywords

  • Fluorescence
  • Sensor
  • Iron(III)
  • Ratiometric

Cite this

Casanueva Marenco, Maria Jose ; Fowley, Colin ; Hyland, Barry W. ; Hamilton, Graham R. C. ; Galindo-Riano, Dolores ; Callan, John F. / A new use for an old molecule: N-phenyl-2-(2-hydroxynaphthalen-1-ylmethylene)hydrazinecarbothioamide as a ratiometric `Off-On' fluorescent probe for iron. 2012 ; Vol. 53, No. 6. pp. 670-673.
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abstract = "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.",
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A new use for an old molecule: N-phenyl-2-(2-hydroxynaphthalen-1-ylmethylene)hydrazinecarbothioamide as a ratiometric `Off-On' fluorescent probe for iron. / Casanueva Marenco, Maria Jose; Fowley, Colin; Hyland, Barry W.; Hamilton, Graham R. C.; Galindo-Riano, Dolores; Callan, John F.

Vol. 53, No. 6, 02.2012, p. 670-673.

Research output: Contribution to journalArticle

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AU - Casanueva Marenco, Maria Jose

AU - Fowley, Colin

AU - Hyland, Barry W.

AU - Hamilton, Graham R. C.

AU - Galindo-Riano, Dolores

AU - Callan, John F.

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AB - 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.

KW - Fluorescence

KW - Sensor

KW - Iron(III)

KW - Ratiometric

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