Porphine

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Porphine

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Template:Longitem	C20H14N4
Molar mass	310.35196 g/mol
Appearance	Dark red, shiny leaflets
Melting point	Template:Chembox CalcTemperatures

Porphine or porphin is an organic compound of empirical formula Template:Chem2. It is heterocyclic and aromatic. The molecule is a flat macrocycle, consisting of four pyrrole-like rings joined by four methine bridges, which makes it the simplest of the tetrapyrroles.

The nonpolar tetrapyrrolic ring structure of porphine means it is poorly soluble in most organic solvents and hardly water soluble. As a result, porphine is mostly of theoretical interest. It has been detected in GC-MS of certain fractions of Piper betle.

Porphine derivatives: porphyrins

Substituted derivatives of porphine are called porphyrins. Many porphyrins are found in nature with the dominant example being protoporphyrin IX. Many synthetic porphyrins are also known, including octaethylporphyrin and tetraphenylporphyrin.

• Common porphyrins
• Derivatives of protoporphyrin IX are common in nature, the precursor to hemes.
  Derivatives of protoporphyrin IX are common in nature, the precursor to hemes.
• Octaethylporphyrin (H2OEP) is a synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, OEP2− is highly symmetrical.
  Octaethylporphyrin (H₂OEP) is a synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, OEP²⁻ is highly symmetrical.
• Tetraphenylporphyrin (H2TPP)is another synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, TPP2− is highly symmetrical. Another difference is that its methine centers are occupied by phenyl groups.
  Tetraphenylporphyrin (H₂TPP)is another synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, TPP²⁻ is highly symmetrical. Another difference is that its methine centers are occupied by phenyl groups.

File:Porphin resonance structures.PNG

Two resonance structures of porphine.