Tetraphenylporphyrin

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Tetraphenylporphyrin

Tetraphenylporphyrin | 917-23-7

Catalog Number A14-0038
Category Calcium, Chloride Indictors and Other indicators
Molecular Formula C44H30N4
Molecular Weight 614.752
Catalog Number Size Price Quantity
A14-0038 -- $--

Product Introduction

Tetraphenylporphyrin is a photosensitizer that is commonly used to form complexes with metals. Tetraphenylporphyrin complexes are inhibitors of microtubule assembly in human cervix carcinoma cells.

Chemical Information

Synonyms 5,10,15,20-(tetraphenyl)porphyrin
Purity >98.0%(HPLC)
IUPAC Name 5,10,15,20-tetraphenyl-21,23-dihydroporphyrin
Canonical SMILES C1=CC=C(C=C1)C2=C3C=CC(=C(C4=CC=C(N4)C(=C5C=CC(=N5)C(=C6C=CC2=N6)C7=CC=CC=C7)C8=CC=CC=C8)C9=CC=CC=C9)N3
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/h1-28,45-46H
InChI Key AQPPOLXYUQPDOD-UHFFFAOYSA-N
Appearance Orange to Brown to Dark purple powder to crystal
  • Product Specification
  • Application
Storage Store at -20°C
Signal Warning
GHS Hazard Statements H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal] H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
Precautionary Statement Codes P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.)

Tetraphenylporphyrin (TPP) is a synthetic organic compound that belongs to the porphyrin class of molecules. Porphyrins are highly conjugated cyclic tetrapyrrole structures, which play essential roles in biological systems, such as in hemoglobin and chlorophyll. TPP is characterized by its robust and planar aromatic structure consisting of a porphyrin core bonded to four phenyl groups at the meso-positions. This configuration results in a compound with high thermal stability and intense absorbance in the visible region, attributed to its extensive π-conjugation system. The chemical stability and versatility of TPP make it a valuable tool in various scientific research and technological fields.

One of the key applications of Tetraphenylporphyrin is in the field of photodynamic therapy (PDT). PDT is a treatment modality that utilizes photosensitizers, like TPP, to generate reactive oxygen species upon light activation, which can effectively target and destroy cancerous cells. Due to TPP’s strong absorption in the visible region, it is well-suited for this purpose, allowing it to be activated by light sources in the clinically useful range. The ability of TPP to selectively accumulate in tumor cells enhances its effectiveness and reduces damage to surrounding healthy tissues. This property makes TPP an attractive candidate for further development in anti-cancer therapies.

In addition to its medical applications, Tetraphenylporphyrin is prominently used as a catalyst in chemical reactions. Its structure can be modified to incorporate metal ions into the central cavity of the porphyrin ring, resulting in metalloporphyrins. These metalloporphyrins act as efficient catalysts in various oxidation and reduction reactions, such as in industrial processes for the synthesis of fine chemicals and pharmaceuticals. The catalytic activities of TPP derivatives are highly regarded due to their ability to mimic natural enzymes, providing high selectivity and efficiency while operating under mild conditions.

Tetraphenylporphyrin also finds application in the field of material science, particularly in the development of organic electronic devices. Its unique electronic properties, stemming from the extensive π-conjugation, allow TPP to be utilized in organic solar cells and light-emitting diodes (OLEDs). In organic photovoltaics, TPP derivatives can act as effective light-harvesting materials that improve the efficiency of solar energy conversion. Similarly, in OLEDs, TPP can function as a luminescent material, offering the advantages of flexible displays and a broad color range. These applications underscore TPP’s potential in advancing the technology of organic electronics.

Moreover, Tetraphenylporphyrin is widely employed as a sensor material due to its sensitive optical and electronic properties. TPP-based sensors can detect a variety of environmental and biological analytes, including gases, metal ions, and biomolecules. The sensitivity of TPP to changes in its environment, particularly through alterations in its spectral properties, allows for the development of highly precise and selective sensing devices. These sensors are valuable in environmental monitoring, medical diagnostics, and other areas where detecting trace amounts of substances is crucial. With ongoing research, TPP continues to expand its role as a versatile component in sensor technology development.

Computed Properties

XLogP3 10.4
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 2
Rotatable Bond Count 4
Exact Mass 614.24704697 g/mol
Monoisotopic Mass 614.24704697 g/mol
Topological Polar Surface Area 57.4Ų
Heavy Atom Count 48
Formal Charge 0
Complexity 851
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes

Literatures

PMIDPublication DateTitleJournal
8164251 1994-04-15 Three-dimensional structure-activity analysis of a series of porphyrin derivatives with anti-HIV-1 activity targeted to the V3 loop of the gp120 envelope glycoprotein of the human immunodeficiency virus type 1 Journal of medicinal chemistry

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