Octaethylporphyrin Explained

Octaethylporphyrin (H2OEP) is an organic compound that is a relative of naturally occurring heme pigments. The compound is used in the preparation of models for the prosthetic group in heme proteins. It is a dark purple solid that is soluble in organic solvents. As its conjugate base OEP2-, it forms a range of transition metal porphyrin complexes. When treated with ferric chloride in hot acetic acid solution, it gives the square pyramidal complex Fe(OEP)Cl.[1] It also forms the square planar complexes Ni(OEP) and Cu(OEP).

Contrast with other porphyrins

Unlike complexes of the naturally occurring porphyrins, OEP complexes have four-fold symmetry, which simplifies spectroscopic analysis. In contrast to tetraphenylporphyrin and related analogues, H2OEP features unprotected meso positions. In this way, it is a more accurate model for naturally occurring porphyrins.

Synthesis

H2OEP is prepared by condensation of 3,4-diethylpyrrole with formaldehyde.[2]

References

  1. Chang, C. K. . DiNello, R. K. . Dolphin, D.. . Iron Porphines . 1980 . 20 . 147 . 10.1002/9780470132517.ch35.
  2. 3,4-Diethylpyrrole and 2,3,7,8,12,13,17,18-Octaethylporphyrin. Jonathan L.. Sessler. Azadeh. Mozaffari. Martin R.. Johnson. Org. Synth.. 1992. 70. 68. 10.15227/orgsyn.070.0068.