Influence of bulky pyrrolyl substitent on the physicochemical properties of porphyrazines

• Syntheses of porphyrazines possessing 2,5–diphenylpyrrol-1-yl groups are reported.
• Physicochemical properties and solid-state structure of porphyrazines are discussed.
• Spin state of iron ion inside the core of iron(II) porphyrazine was investigated.

The synthesis and characterization of porphyrazines possessing 2,5–diphenylpyrrol-1-yl and dimethylamino peripheral groups and their precursors are shown. Bulky pyrrolyl substituents influenced the physicochemical properties and solid-state structure of novel porphyrazines and did not hamper the formation of the porphyrazine associates in solution and solid-state. Occurrence of centrosymmetric dimers in single crystal X-ray structure of magnesium(II) porphyrazine with Mg⋯Mg distance of ca. 11.2 Å, impacted by interdigitation of the phenyl substituents, was noticed. In addition, an iron(II) porphyrazine derivative was investigated. The importance of Mössbauer spectroscopy in the assessment of valence and spin state of the iron ion inside the core of the iron(II) porphyrazine is shown.

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