A new water-soluble phosphorus-dipyrromethene and phosphorus-azadipyrromethene dye: PODIPY/aza-PODIPY

Chemistry. 2015 Apr 13;21(16):6079-82. doi: 10.1002/chem.201406535. Epub 2015 Mar 4.

Abstract

PODIPY and aza-PODIPY have been successfully prepared by the treatment of dipyrromethene and azadipyrromethene with POCl3 in the presence of Et3 N. The new PODIPY and aza-PODIPY dyes are found to have photophysical properties. PODIPY and aza-PODIPY are water-soluble, and aza-PODIPY is suited for labeling living Hep-2 cells for imaging assays in the near-infrared region. Molecular orbital calculations show that the increase in the HOMO-LUMO band gap for the lowest energy absorption bands is observed in the new phosphorus-containing aza-PODIPY, and the HOMO and LUMO energies of aza-PODIPY are found to be higher than those of aza-BODIPY.

Keywords: PODIPY; fluorescent probes; phosphorus; photophysical properties; water soluble.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemistry*
  • Fluorescent Dyes / chemistry*
  • Hep G2 Cells
  • Humans
  • Models, Molecular
  • Optical Imaging
  • Organophosphorus Compounds / chemistry*
  • Porphobilinogen / analogs & derivatives*
  • Porphobilinogen / chemistry
  • Solubility
  • Water / chemistry

Substances

  • Aza Compounds
  • Fluorescent Dyes
  • Organophosphorus Compounds
  • dipyrromethene
  • Water
  • Porphobilinogen