A Colorimetric and Fluorimetric Chemodosimeter for Copper Ion Based on the Conversion of Dihydropyrazine to Pyrazine

Chem Asian J. 2016 Jan;11(1):136-40. doi: 10.1002/asia.201500932. Epub 2015 Oct 2.

Abstract

In this research, we successfully synthesized and fully characterized the new compound 5,8,13,16,21,24-hex-(triisopropylsilyl)ethynyl)-6,23-dihydro-6,7,14,15,22,23-hexaza-trianthrylene (HHATA, brown color in a mixed solvent of CH2 Cl2 /CH3 CN 1:1, v/v, weakly blue fluorescent), which can be easily oxidized to 5,8,13,16,21,24-hex-(triisopropylsilyl)ethynyl)-6,7,14,15,22,23-hexazatrianthrylene (HATA) (yellow color in CH2 Cl2 /CH3 CN 1:1, v/v), red fluorescent) by Cu(2+) ions. This reaction only proceeds efficiently in the presence of Cu(2+) ions when compared with other common metal ions such as Fe(3+) , Co(2+) , Mn(2+) , Hg(2+) , Ni(2+) , Pb(2+) , Ag(+) , Mg(2+) , Ca(2+) , K(+) , Na(+) , and Li(+) . Our result suggests that this reaction can be developed as an effective method for the detection of Cu(2+) ions.

Keywords: azaacene; copper ions; oxidation; pyrazine; sensors.

MeSH terms

  • Anthracenes / chemical synthesis
  • Anthracenes / chemistry*
  • Colorimetry*
  • Copper / analysis*
  • Fluorometry*
  • Ions / analysis
  • Models, Molecular
  • Molecular Structure
  • Oxidation-Reduction
  • Pyrazines / chemical synthesis*
  • Pyrazines / chemistry*

Substances

  • 3,16,21,24-hex-(triisopropylsilyl)ethynyl)-6,23-dihydro-6,7,14,15,22,23-hexaza-trianthrylene
  • Anthracenes
  • Ions
  • Pyrazines
  • Copper