Pyridylthiazoles: highly luminescent heterocyclic compounds

J Phys Chem A. 2007 Feb 15;111(6):1104-10. doi: 10.1021/jp0672003. Epub 2007 Jan 25.

Abstract

Absorption, fluorescence, and fluorescence excitation spectra of two substituted [(5-methyl-2-pyridine-2'-yl-1,3-thiazole-4-yl)oxy]acetic acid and its methyl ester (2,2'-pyridylthiazoles) are studied at various pH values in aqueous solution. The acid exhibits pKa(1)=2.10+/-0.07 and pKa(2)=3.45+/-0.03, whereas the ester pKa=1.93+/-0.03. The protonation site is the pyridyl-nitrogen. When protonated, the cisoid conformer is the most stable; however, the transoid conformer is more stable in the deprotonated form. Fluorescence quantum yields close to unity are found. Large Stokes shift values are explained by the shortening of the inter-ring bond in the excited state. These compounds may be useful for metal sensing and as laser dyes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemical synthesis
  • Acetates / chemistry*
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / chemistry*
  • Hydrogen-Ion Concentration
  • Luminescence
  • Quantum Theory
  • Sensitivity and Specificity
  • Solutions / chemistry
  • Spectrometry, Fluorescence / methods
  • Spectrophotometry, Ultraviolet / methods
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry*
  • Water / chemistry

Substances

  • 5-methyl-2-pyridine-2'-yl-1,3-thiazole-4-yl-oxyacetic acid
  • Acetates
  • Heterocyclic Compounds
  • Solutions
  • Thiazoles
  • methyl 5-methyl-2-pyridine-2'-yl-1,3-thiazole-4-yl-oxyacetate
  • Water