A novel phosphate chemosensor utilizing anion-induced fluorescence change

Org Lett. 2002 Feb 21;4(4):561-4. doi: 10.1021/ol0171564.

Abstract

[structure: see text] The neutral receptor N,N'-bis[3,5-di[(1-pyrenylmethyl)carbamoyl]benzyl] pyridine-2,6-dicarbamide (2) provides a pseudo-tetrahedron cleft and multiple hydrogen bondings to form a 1:1 complex with phosphate ion in a highly selective manner, by comparison with other anions (F(-), Cl(-), Br(-), SCN(-), AcO(-), NO(3)(-), ClO(4)(-), and HSO(4)(-)). The binding strength can be inferred from the emission intensity ratio of the pyrene monomer (lambda(max) 377 nm) to the excimer (lambda(max) 477 nm). Fluorescence titration, X-ray analysis, and NMR studies support a proposed complexation model.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Fluorescence
  • Fluorescent Dyes
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Phosphates / chemistry*
  • Pyrenes / chemistry*
  • Pyridines / chemistry*
  • Spectrometry, Fluorescence

Substances

  • Fluorescent Dyes
  • Indicators and Reagents
  • N,N'-bis(3,5-di-((1-pyrenylmethyl)carbamoyl)benzyl)pyridine-2,6-dicarbamide
  • Phosphates
  • Pyrenes
  • Pyridines