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Using porphine derivative ligands for the preparation and functionalization of porphyrins

It is hard to overestimate the importance of porphyrins in life sciences.  Chlorophylls, Vitamin B12 and heme (in hemoglobin) are just a few examples of how essential these naturally occurring materials are to life.

Many researchers have focused on synthetic metal porphyrins because of their outstanding properties such as chemical and structural stability, chromaticity, electronic and optical properties, strong aromaticity and rich metal coordination chemistry.

In general, simple metal porphyrins are prepared by the direct interaction of metal salts with corresponding porphyrin ligands. Single porphyrin units allow added functionalization and conjugation in arrays by using alkene or alkyne type linkers, resulting in delocalized electronic structures. This unique characteristic allows porphyrins to play an important role in photovoltaics as near infrared dyes, nonlinear optical materials and electron-conducting molecular wires.^[1-2]   

We offer porphyrin ligands for a variety of synthetic purposes, starting from the standard porphines Octaethylporphyrin (OEP) [07-1550] and Tetraphenylporphyrins (TPP) [07-2160 and 07-2170] to enzymatic porphyrins, such as Coproporphyrin and Uroporphyrin.

07-1550: Octaethylporphine, 97+% OEP	07-2160: meso-Tetraphenylporphine, min. 97% TPP (contains 1-3% chlorin)

OEP and TPP metal complexes are very important materials for every kind of photochemical, electronic and optical applications (Organic and Polymer Light Emitting Diodes (OLED and PLED)as well as dye sensitizers (fluorescent dyes, etc.). Metal porphyrins typically exhibit two sets of absorption bands in the neighborhood of 550 nm and 400 nm.

Metalloporphyrins are used as effective catalysts in almost every research discipline, such as organic chemistry^[3], electrocatalysis^[4] and biocatalysis^[5] to name a few.  Porphyrin-ligands are also of interest in MOF technology, especially if porphyrin linkers are functionalized with carboxylic or pyridine groups in the outer sphere.^[5]

Porphyrins play an extremely important role in various biological systems in which they transport proteins, accept and donate electrons, and catalyze biochemical reactions.  For instance, after a series of reactions, uroporphyrinogen and coproporphyrinogen in the body will automatically oxidize to uroporphyrin (07-3350 and 07-3410) and coproporphyrin (07-0300 and 07-0305).^[6]

In the Coproporphyrin I isomer (07-0300), the four propionic acid side groups are equidistant and the molecule is thus symmetric. In the Coproporphyrin III isomer (07-0305), one of the pyrroles is inverted during the biosynthesis of the porphyrin ring structure, resulting in an asymmetric distribution of methyl and propionic acid side groups of the porphyrin molecule. 

Products mentioned in this blog and related products:

References:

1.       Chem. Soc. Rev., 2015, 44, 943.
2.       Chem. Rev., 2014, 114, 12330.
3.       Org. Lett., 2006, 8, 325.
4.       Int. J. Hydrogen Energ., 2014, 39, 4803.
5.       Acc. Chem. Res., 2014, 47, 1199.
6.       Talanta 143, 2015, 27.