Fluorescent iminodiacetamide derivatives as potential ionophores for optical zinc ion-selective sensors

Nikoleta Urbanová, Mihály Kádár, K. Tóth, Botond Bogáti, Vasil Andruch, I. Bitter

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Fluorescent sensor molecules were synthesized by conjugation of iminodiacetamide derivatives with fluorescent moieties of different structures and their UV-visible and fluorescent properties were characterized in acetonitrile solvent. The fluorescent measurements revealed that the N-(2-naphthyl) and N-phenyl derivatives exhibit a distinct zinc ion-selectivity over alkali and alkaline earth metal ions, while N-(anthrylmethyl) and N-(3-methoxyphenyl) derivatives do not possess any ion-selectivities. In contrast to the fluorescent measurements, all ligands show Zn2+ selectivity over Ca2+ and Mg2+ ions in plasticized PVC membranes using potentiometric signal transduction. This observation found for N-(anthrylmethyl) and N-(3-methoxyphenyl) derivatives can be ascribed to the more hindered interaction between the signalling group of the ionophore and the central metal ion in PVC membranes than in acetonitrile solution upon complexation. From the fluorescent measurements it can also be concluded that the ligands with metal ions form complexes mainly with 2:1 stoichiometry (L 2M). On complex formation a considerable decrease in the fluorescent intensity was observed for all ligands except the N-(anthrylmethyl) derivative, where a 25-30 fold fluorescence enhancement was found, which is explained by the photoinduced electron transfer (PET) mechanism. All ionophores exhibited serious hydrogen ion interference, therefore complexation-induced spectral changes were measured in aprotic acetonitrile solution. 2008

Original languageEnglish
Pages (from-to)727-733
Number of pages7
JournalAnalytical Sciences
Volume24
Issue number6
DOIs
Publication statusPublished - Jun 2008

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Ionophores
Zinc
Ions
Derivatives
Sensors
Metal ions
Ligands
Complexation
Polyvinyl Chloride
Alkaline Earth Metals
Membranes
Signal transduction
Alkalies
Stoichiometry
Protons
Fluorescence
Molecules
Electrons
acetonitrile

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

Fluorescent iminodiacetamide derivatives as potential ionophores for optical zinc ion-selective sensors. / Urbanová, Nikoleta; Kádár, Mihály; Tóth, K.; Bogáti, Botond; Andruch, Vasil; Bitter, I.

In: Analytical Sciences, Vol. 24, No. 6, 06.2008, p. 727-733.

Research output: Contribution to journalArticle

Urbanová, Nikoleta ; Kádár, Mihály ; Tóth, K. ; Bogáti, Botond ; Andruch, Vasil ; Bitter, I. / Fluorescent iminodiacetamide derivatives as potential ionophores for optical zinc ion-selective sensors. In: Analytical Sciences. 2008 ; Vol. 24, No. 6. pp. 727-733.
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