Tetraphenylporphyrin

Tetraphenylporphyrin

Names
Other names 5,10,15,20-Tetraphenylporphin, TPP, H2TPP
Identifiers
CAS Number	917-23-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:52279 N
ChemSpider	10291672 N
ECHA InfoCard	100.011.842
MeSH	C509964
InChI InChI=1S/C44H30N4/c1-5-13-29(14-6-1)41-33-21-23-35(45-33)42(30-15-7-2-8-16-30)37-25-27-39(47-37)44(32-19-11-4-12-20-32)40-28-26-38(48-40)43(31-17-9-3-10-18-31)36-24-22-34(41)46-36/h1-28,45,48H/b41-33-,41-34-,42-35-,42-37-,43-36-,43-38-,44-39-,44-40- N Key: YNHJECZULSZAQK-LWQDQPMZSA-N N InChI=1/C44H30N4/c1-5-13-29(14-6-1)41-33-21-23-35(45-33)42(30-15-7-2-8-16-30)37-25-27-39(47-37)44(32-19-11-4-12-20-32)40-28-26-38(48-40)43(31-17-9-3-10-18-31)36-24-22-34(41)46-36/h1-28,45,48H/b41-33-,41-34-,42-35-,42-37-,43-36-,43-38-,44-39-,44-40- Key: YNHJECZULSZAQK-LWQDQPMZBQ
SMILES c1ccc(cc1)/c/2c\3/nc(/c(c/4\[nH]/c(c(\c5n/c(c(\c6[nH]c2cc6)/c7ccccc7)/C=C5)/c8ccccc8)/cc4)/c9ccccc9)C=C3
Properties
Chemical formula	C44H30N4
Molar mass	614.74 g/mol
Appearance	dark purple solid
Density	1.27 g/cm3
Solubility in water	insoluble in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Tetraphenylporphyrin, abbreviated TPP or H₂TPP, is a synthetic heterocyclic compound that resembles naturally occurring porphyrins. Porphyrins are dyes and cofactors found in hemoglobin and and are related to chlorophyll and vitamin B₁₂. The study of naturally occurring porphyrins is complicated by their low symmetry and the presence of polar substituents. Tetraphenylporphyrin is hydrophobic, symmetrically substituted, and easily synthesized. The compound is a dark purple solid that dissolves in nonpolar organic solvents such as chloroform and benzene.

Tetraphenylporphyrin was first synthesized in 1935 by Rothemund, who caused benzaldehyde and pyrrole to react in a sealed bomb at 150 °C for 24 h. Adler and Longo modified the Rothemund method by allowing benzaldehyde and pyrrole to react for 30 min in refluxing propionic acid (141 °C) open to the air:

Despite low yields, the synthesis of H₂TPP is a common experiment in university teaching labs.

The conjugate base of the porphyrin, TPP²⁻, belongs to the symmetry group D_4h while its hydrogenated counterpart H₂(TPP) is D_2h. Unlike natural porphyrins, H₂TPP is substituted at the oxidatively sensitive "meso" carbon positions, and hence the compound is sometimes called meso-tetraphenylporphyrin. Another synthetic porphyrin, octaethylporphyrin (H₂OEP) does have a substitution pattern that is biomimetic. Many derivatives of TPP and OEP are known, including those prepared from substituted benzaldehydes. One of the first functional analogues of myoglobin was the ferrous derivative of the "picket fence porphyrin," which is structurally related to Fe(TPP), being derived via the condensation of 2-nitrobenzaldehyde and pyrrole.

Sulfonated derivatives of TPP are also well known to give water-soluble derivatives, e.g. tetraphenylporphine sulfonate: