Isoquinoline-based TQEN family as TPEN-derived fluorescent zinc sensors

Inorg Chem. 2008 Aug 18;47(16):7295-301. doi: 10.1021/ic8002614. Epub 2008 Jul 22.

Abstract

The hexadentate nitrogen ligands 1-isoTQEN ( N,N,N',N'-tetrakis(1-isoquinolylmethyl)ethylenediamine) and 3-isoTQEN ( N,N,N',N'-tetrakis(3-isoquinolylmethyl)ethylenediamine) have been prepared. The structures of these ligands are based on that of TPEN ( N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine). The introduction of a benzene ring into TPEN affords fluorescence ability upon zinc-ion binding. Compared to the quinoline isomer TQEN, isoquinoline derivatives 1-isoTQEN and 3-isoTQEN exhibit a lower-energy shift in the excitation and emission wavelengths and an enhanced fluorescence intensity, probably because of the energy-transfer mechanism between adjacent isoquinoline rings. Importantly, an increase in the Zn (2+)/Cd (2+) discriminating ability and a reduction in the background fluorescence induced by pH were also achieved for isoquinoline derivatives. The zinc-ion-induced fluorescence of these isoTQENs was not quenched by an addition of TPEN, which demonstrates the significantly high zinc-ion binding ability of these isoTQEN ligands.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Ethylenediamines / chemistry*
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Hydrogen-Ion Concentration
  • Isoquinolines / chemistry*
  • Ligands
  • Quinolines / chemistry
  • Spectrometry, Fluorescence
  • Spectrophotometry, Ultraviolet
  • Zinc / chemistry*

Substances

  • Ethylenediamines
  • Fluorescent Dyes
  • Isoquinolines
  • Ligands
  • N,N,N',N'-tetrakis(1-isoquinolylmethyl)ethylenediamine
  • Quinolines
  • quinoline
  • Zinc
  • isoquinoline
  • N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine