Highly selective colorimetric detection of cyanide anions in aqueous media by triphenylamine and phenanthro(9,10-d)imidazole based probes

Photochem Photobiol Sci. 2017 Feb 15;16(2):255-261. doi: 10.1039/c6pp00345a.

Abstract

Two novel fluorescent probes based on triphenylamine (TPC) and phenanthro(9,10-d-imidazole) (PITP) have been synthesized and studied as cyanide selective indicators in aqueous media. Complete colour bleaching was observed due to the nucleophilic addition of cyanide to the 2-vinylmalononitrile of TPC, which results in the disruption of the extended conjugation and turns off the intramolecular charge transfer (ICT) process. Furthermore, a visible color change was observed with a large Stokes shift (108 nm) upon the addition of cyanide anions to PITP, due to the formation of hydrogen bonding between the CN- anion and -NH of PITP, which increased the electron density on the donor moiety and induced strong ICT.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry*
  • Anions / chemistry
  • Colorimetry*
  • Cyanides / analysis*
  • Fluorescent Dyes / chemistry
  • Hydrogen Bonding
  • Imidazoles / chemistry
  • Light
  • Magnetic Resonance Spectroscopy
  • Phenanthrenes / chemistry*
  • Quantum Theory
  • Spectrometry, Fluorescence
  • Ultraviolet Rays
  • Water / chemistry

Substances

  • Aniline Compounds
  • Anions
  • Cyanides
  • Fluorescent Dyes
  • Imidazoles
  • Phenanthrenes
  • Water