A modified cyclen azaxanthone ligand as a new fluorescent probe for Zn2+

Dalton Trans. 2013 Sep 14;42(34):12157-64. doi: 10.1039/c3dt51216a. Epub 2013 Jul 9.

Abstract

A new cyclen derivative L, bearing a methyl-chromeno-pyridinylidene hydrazone moiety, was synthesized and studied in MeOH, as potential fluorescent "OFF-on-ON" sensors for Zn(ii). Photophysical properties of this ligand being PET regulated, L was only weakly emissive in the absence of metal ions (OFF). L fluorescence was increased modestly upon addition of one equivalent of Zn(II), and further increased upon addition of a second equivalent. Therefore, Zn : L behaved as a highly sensitive ON sensor for zinc. This efficiency was correlated to Zn(II) coordination via the hydrazone moiety of the fluorophore, producing an efficient CHelation-Enhanced Fluorescence (CHEF) effect. A complementary theoretical study carried out with DFT calculations further elucidated the optical properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclams
  • Fluorescent Dyes / chemistry*
  • Heterocyclic Compounds / chemistry*
  • Ions / chemistry
  • Ligands
  • Quantum Theory
  • Spectrometry, Fluorescence*
  • Zinc / analysis*

Substances

  • Cyclams
  • Fluorescent Dyes
  • Heterocyclic Compounds
  • Ions
  • Ligands
  • cyclen
  • Zinc