Highly selective colorimetric and electrochemical Pb2+ detection based on TTF-pi-pyridine derivatives

J Org Chem. 2005 Nov 25;70(24):9727-34. doi: 10.1021/jo051091r.

Abstract

[reaction: see text] The pyridineethenyl-substituted tetrathiafulvalene (TTF) compounds, 4-(4-pyridineethenyl)tetrathiafulvalene (1a) and 4,4'(5')-[bis-(4-pyridineethenyl)]tetrathiafulvalene (2a) together with the styryl-substituted TTF compounds, 4-styryltetrathiafulvalene (1b) and 4,4'(5')-bis-styryltetrathiafulvalene (2b), have been designed and synthesized. All these compounds exhibit strong absorption bands in the range of 370 to 550 nm, which are assigned to the intramolecular charge-transfer transition from the HOMO in TTF to the LUMO in the pyridyl or phenyl group. Compared to compounds 1b and 2b, the pyridineethenyl-substituted TTF compounds 1a and 2a show remarkable sensing and coordinating properties to Pb2+. With the addition of micromolar concentrations of Pb2+ to the solution, 1a or 2a displays dramatic changes in the UV-vis absorption spectrum, 1H NMR spectrum, and redox property.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Absorption
  • Colorimetry
  • Electrochemistry
  • Ethylenes / chemistry*
  • Heterocyclic Compounds / chemistry*
  • Lead / chemistry*
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Structure
  • Oxidation-Reduction
  • Pyridines / chemistry*
  • Sensitivity and Specificity
  • Spectrophotometry, Ultraviolet / methods

Substances

  • Ethylenes
  • Heterocyclic Compounds
  • Pyridines
  • Lead
  • tetrathiafulvalene