meso-Tetra(4-carboxyphenyl)porphine

meso-Tetra(4-carboxyphenyl)porphine meso-Tetraphenylporphine- 4,4′,4”,4”’-tetracarboxylic acid CAS: 14609-54-2 MDL: MFCD00064860

SDS

Molecular weight: 790.8 g/mol

Molecular Formula: C₄₈H₃₀N₄O₈

CAS Number: 14609-54-2

Storage: Store at room temperature, protect from light.

Synonyms: 14609-54-2, meso-Tetra(4-carboxyphenyl)porphine, TCPP, 4,4,4,4-(Porphine-5,10,15,20-tetrayl)tetrakis(benzoic acid), Tetrakis(4-carboxyphenyl)porphyrin, Tetracarboxyphenylporphine, MFCD00064860, Tetrakis (4-carboxyphenyl) porphyrin, UNII-E9892W6IMC, CHEMBL374342, E9892W6IMC, 4-[10,15,20-tris(4-carboxyphenyl)-21,23-dihydroporphyrin-5-yl]benzoic acid, 4,4′,4”,4”’-(Porphine-5,10,15,20-tetrayl)tetrakis(benzoic acid), 5,10,15,20-Tetrakis(4-carboxyphenyl)-21H,23H-porphine, MTCPP, YSZC167, SCHEMBL709532, tetra(4-carboxyphenyl)porphine, CCRIS 8701, HSDB 8470

Field of Interest: Metal-Organic-Frameworks MOF’S, Sensors,

Background: meso-Tetra(4-carboxyphenyl)porphine,TCPP is a synthetic porphyrin specialty chemical bearing four carboxy groups which make this compound extremely useful for the construction of metal-organic-frameworks^1,2. TCPP was used to synthesize a porphyrinic zirconium-based MOF that could be used as a fluorescence sensor for Cd(II) and Br- ions³. TCPP was used as a light-addressable potentiometric sensor for DNA methylation⁴. TCPP was found to bind to CD320, the cellular receptor for cobalamin/transcobalamin II in cancer cells⁵. TCPP was used to produce a porphyrin supramolecular array along with meso-tetrakis(4-dimethylamino)porphine on a Au(111) surface⁶. TCPP has been used as a photosensitizer on nanoparticulate TiO2 for solar energy conversion⁷.

References:

1.) Rajasree, S.S., Li, X., Deria, P.; Physical Properties of Porphyrin-based crystalline metal-organic frameworks. Communications Chemistry 4, 47, 2021. https://doi.org/10.1038/s42004-021-00484-4

2.) Chen, J., Zhu, Y., Kaskel, S.; Porphyrin-Based Metal_Organic Frameworks for Biomedical Applications. Angew. Chemie. Int. Ed. 2021, 60, 5010-5035. https://doi.org/10.1002/anie.201909880

3.) Moradi, E., Rahimi, R., Farahani, Y.D., Safarifard, V.; Porphyrinic zirconium-based MOF with exposed pyrrole Lewis base site as a luminescent sensor for highly selective sensing of Cd2+ and Br- ions and THF small molecule. Journal of Solid State Chemistry 2020, 282, 121103. https://doi.org/10.1016/j.jssc.2019.121103

4.) Jia, Y., Li, F., Jia, T., Wang, Z.; Meso-tetra(4-carboxyphenyl)porphine-Enhanced DMA Methylation Sensing Interface on a Light-Addressable Potentiometric Sensor. ACS Omega 2019, 4, 7, 12567-12574. https://doi.org/10.1021/acsomega.9b00980

5.) Elzi, D.J., Bauta, W.E., Sanchez, J.R., Das, T., Mogare, S., Fatland, P.Z., Iza, M., Pertsemlidis, A., Rebel, V.T.; Identification of a novel mechanism for meso-tetra(4-carboxyphenyl) porphyrin (TCPP) uptake in cancer cells. The FASEB Journal. 2021;35:e21427. https://doi.org/10.1096/fj.202000197R

6.) Sanchez-Munoz, E., Garate-Morales, J.L, Sandoval-Lira, J., Hernandez-Perez, J.M., Aguilar-Sanchez, R.; Porphyrin Supramolecular Arrays Fromed by Weakly Intereacting Meso-Functional Groups on Au(111). Molecules 2019, 24(18), 3326; https://doi.org/10.3390/molecules24183326

7.) Cherian, S., Wamser, C.C.; Adsorption and Photoactivity of Tetra(4-carboxyphenyl)porphyrin (TCPP) on Nanoparticulate TiO2. J. Phys. Chem. B 2000, 104, 15, 3624–3629. https://doi.org/10.1021/jp994459v