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.

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