The Facile Synthesis and Characterization of Novel Cationic Metallated and Nonmetallated Tetrapyridino Porphyrazines Having Different Metal Centers

Abstract

A porphyrazine and a series of tetracationic porphyrazines, metallated and nonmetallated, were synthesized. The neutral tetrapyridino porphyrazine was obtained in a yield of 45%. The tetracationic nonmetallated tetraethanoltetrapyridino porphyrazinium iodide was obtained in a yield of 79%. The metallated porphyrazines are (Mn⁺², Cu⁺², Co⁺², Zn⁺²) = M. M‐Tetraethanoltetrapyridino porphyrazinium iodide was obtained in a yield of 78%, 69%, 75%, and 72%, respectively. The porphyrazine and the tetracationic porphyrazines, nonmetallated and metallated, were characterized by elemental analysis, ESI‐MS, MALDI‐MS, FTIR, and UV‐VIS.

Keywords:

• Metallated
• Nonmetallated
• Tetracationic porphyrazines

AcknowleDgments

This work was supported by the Ramirez‐Miller Foundation. The Quatro mass spectrometer was purchased in part with a grant from the Division of Research Resources, National Institute of Health (RR 07141). The 70‐SE‐4F mass spectrometer was purchased in part with funds from the National Institute of General Medical Sciences (GM 27029). The Voyager‐DE STR mass spectrometer was purchased in part with a grant from the Division of Research Resources, National Institute of Health (RR 11966). We also thank Prof. John Sowa for his careful reading of this manuscript.