After their discovery by Rogers in the 1940s, azadipyrromethenes (ADPM) have emerged as interesting dyes showing luminescence and absorption bands in the long-wavelength region of the visible spectrum. To date, no ADPMs have been synthesized bearing pyridine rings at the proximal position (see scheme below), so we decided to generate these compounds in order to extend our knowledge of ADPM chemistry. Structural modification on the phenyl ring substituents (R groups) reveals an interesting trends in the physical properties of these compounds. Several free base ADPMs with proximal pyridines and a few examples of transition metal complexes have been synthesized and characterized by 1H and 13C NMR spectroscopy, X-ray crystallography, UV-Visible and FT-IR spectroscopy, and mass spectrometry. The influence of R groups was also observed and it was found that electron donating/withdrawing ability can affect the stability of free ADPM ligands.

New azadipyrromethenes bearing pyridine rings: Synthesis and characterization

246th National Meeting (2013)

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