An extremely stable host-guest complex that functions as a fluorescence probe for calcium ions

Chemistry. 2006 Jun 2;12(17):4594-9. doi: 10.1002/chem.200600090.

Abstract

Herein, we report a crown ether based molecular cage that forms extremely stable supramolecular complexes with dimethyldiazapyrenium (DMDAP) ions in CD(3)CN through the collaboration of multiple weak C-HO hydrogen bonds. The very strong binding affinity in this host-guest system allows the molecular cage to bleach the fluorescence signal of DMDAP substantially in equimolar solutions at concentrations as low as 1 x 10(-5) M. Remarkably, a 1x10(-5) M equimolar solution of the molecular cage and DMDAP is highly selective toward Ca(2+) ions-relative to other biologically important Li(+), Na(+), K(+), and Mg(2+) ions-and causes a substantial increase in the fluorescence intensity of the solution. As a result, this molecular cage/DMDAP complex behaves as a supramolecular fluorescence probe for the detection of Ca(2+) ions in solution.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemistry
  • Calcium / analysis*
  • Crown Ethers / chemical synthesis
  • Crown Ethers / chemistry*
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Hydrogen Bonding
  • Ions / analysis
  • Pyridinium Compounds / chemistry
  • Solutions / chemistry

Substances

  • Aza Compounds
  • Crown Ethers
  • Fluorescent Dyes
  • Ions
  • Pyridinium Compounds
  • Solutions
  • dimethyldiazapyrenium
  • Calcium