87345-22-0

Basic information

• Product Name: 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin
• Synonyms: 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin;Phenol, 4-(10,15,20-triphenyl-21H,23H-porphin-5-yl)- 4-(10,15,20-triphenylporphyrin-5-yl)phenol;5-(4-hydroxyphenyl)-10,15,20-triphenyl porphine
• CAS NO: 87345-22-0
• Molecular Formula: C₄₄H₃₀N₄O
• Molecular Weight: 630.74
• Mol File: 87345-22-0.mol

Chemical Properties

• Appearance: /
• Density: 1.29g/cm³
• Refractive Index: 1.709
• CAS DataBase Reference: 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin(CAS DataBase Reference)
• NIST Chemistry Reference: 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin(87345-22-0)
• EPA Substance Registry System: 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin(87345-22-0)

Safety Data

• Hazardous Substances Data: 87345-22-0(Hazardous Substances Data)

Usage

Uses

Used in Photodynamic Therapy:
5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin is used as a photosensitizer in photodynamic therapy for its ability to absorb light and generate reactive oxygen species, which can induce cell death in targeted tissues, making it a potential treatment for various types of cancer.
Used in Imaging Applications:
In the field of imaging, 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin is used as a contrast agent due to its strong light absorption and fluorescence properties, which can enhance the visualization of biological structures and processes.
Used in Sensing Applications:
5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin is utilized as a sensing molecule for detecting various analytes, including gases, ions, and biomolecules, owing to its sensitivity to environmental changes and its ability to undergo fluorescence or absorption changes upon interaction with target species.
Used in Materials Science:
In materials science, 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin is employed in the development of functional materials, such as solar cells, light-emitting diodes, and molecular electronics, due to its light-harvesting capabilities and electronic properties.
Used in Pharmaceutical Industry:
5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin is used as a drug candidate in the pharmaceutical industry for its potential therapeutic effects in various diseases, including cancer, neurological disorders, and infectious diseases, based on its ability to modulate biological processes and interact with specific targets.

InChI:InChI=1/C44H30N4O/c49-32-18-16-31(17-19-32)44-39-26-24-37(47-39)42(29-12-6-2-7-13-29)35-22-20-33(45-35)41(28-10-4-1-5-11-28)34-21-23-36(46-34)43(30-14-8-3-9-15-30)38-25-27-40(44)48-38/h1-27,45,48-49H/b41-33-,41-34-,42-35-,42-37-,43-36-,43-38-,44-39-,44-40-

Upstream product

• 109-97-7 pyrrole 
• 100-52-7 benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 107798-98-1 5-phenyldipyrromethane 
• 99522-34-6 4-[(tetrahydro-2H-pyran-2-yl)oxy]iodobenzene 
• 67066-09-5 5-bromo-10,20-dihexyl-15-phenylporphyrin (5) 

Downstream Products

• 81046-68-6 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin copper 

Relevant articles and documents

Selective synthesis and biological activity of triazine-porphyrins as potential anti-cancer agents

Ten new triazine-porphyrin derivatives were synthesized using a simple one-pot procedure from the reaction of tetraphenylporphyrin bearing a hydroxyl group with 2,4,6-trichloro-1,3,5-triazine, and then with amines or alcohols. The structures of the products were characterized by 1H NMR, LC/MS, UV-vis and elemental analysis. The cytotoxic activity of the triazine-porphyrin derivatives was evaluated in vitro against MCF-7 cell. All new compounds showed similar activity against MCF-7 cells in the absence of light when compared to 5-fluorouracil and hematoporphyrin.

Design of novel well-defined oligothiophenes bearing donor-acceptor groups (pyrene-porphyrin): Synthesis, characterization, optical properties and energy transfer

Novel thiophene monomers containing porphyrin units attached via di(ethylene glycol) and tetra(ethylene glycol) spacers were synthesized: 3-methyl-4- (4- (1- (5-phenyl-10,15,20-triphenylporphyrin)) diethoxy) thiophene (M2PPh) and 3-methyl-4- (4- (1- (5-ph

Intramolecular Electron Transfer in Donor-Acceptor Systems. Porphyrins Bearing Trinitroaryl Acceptor Group

Porphyrins bearing picryl group in ortho, meta, and para positions of one of the mesoaryl groups of tetraphenylporphyrin (TPP) have been synthesized in the free-base form.The metal derivatives of the free-base picrylporphyrins (PPc) have been prepared.The broadened Soret absorption, the decreased optical absorbance values of Q bands, and the reduced singlet emission quantun yields of PPc indicate the existence of intramolecular interaction.The extent of this interaction is found to be greater than those observed for the intermolecular systems and varies with the position at which the picryl moiety is attached to the porphyrin as ortho > meta > para.The energies of the redox states, E(CT) of P+Pc-, calculated from the electrochemical redox potentials depend on the nature of the metal ion as free-base PPc > CuPPc > ZnPPc.The nature of intramolecular interaction between the picryl moiety and porphyrin unit is essentially ?-? (CT).Conclusive evidence for light-induced electron transfer in ZnPPc is presented from EPR studies.The decay profiles of the EPR signals vary with the position of the picryl moiety as ortho para meta.Computer simulation of structures substantiated by the 1H NMR results point out the restricted conformational freedom of the picryl moiety in ZnPPc.Arguments based on symmetry considerations of HOMO of the excited singlet state PPc and LUMO of picryl group indicate plane-to-plane orientation of the donor and acceptor in the picrylporphyrins.

Photo-Enhanced Antimicrobial Activity of Polymers Containing an Embedded Photosensitiser

This work presents the synthesis of a novel photosensitive acrylate monomer for use as both a self-catalyst in the photoinduced electron/energy transfer–reversible addition fragmentation chain transfer (PET-RAFT) polymerisation process and a photosensitis

Red Light-Triggered Intracellular Carbon Monoxide Release Enables Selective Eradication of MRSA Infection

Carbon monoxide (CO) is an important gaseous signaling molecule. The use of CO-releasing molecules such as metal carbonyls enables the elucidation of the pleiotropic functions of CO. Although metal carbonyls show a broad-spectrum antimicrobial activity, i

The synthesis of star-shaped poly(: N-isopropylacrylamide) with two zinc porphyrins as the core and end groups via ATRP and "cLICK" chemistry and a photocatalytic performance study

Through the cooperation of atom transfer radical polymerization (ATRP) and the click reaction, star-shaped poly(N-isopropylacrylamide), namely, (ZnTHPP-(PNIPAM-ZnTPP)4) with 5,10,15,20-tetra(4-(2-bromoisobutoxy)phenyl)-21H,23H-zincporphyrin (ZnTHPP-4Br) as the core group and 5-(4-propargyloxyphenyl)-10,15,20-triphenylzinc-21H,23H-porphyrin (ZnTPP-Py) as the end group was prepared, and it was used as a photocatalyst for the degradation of Rhodamine B under visible light irradiation. The structure of the star-shaped polymer was characterized by FT-NIR,1H NMR, UV-Vis and GPC analyses. The photocatalytic property study indicated that ZnTHPP-(PNIPAM-ZnTPP)4 had higher photocatalytic activity than the polymer ZnTHPP-(PNIPAM-Br)4 before the click reaction and could be recycled by warming.

Synthesis and photophysical properties of novel pyrene-metalloporphyrin dendritic systems

A novel series of dendronized porphyrins bearing pyrene units in the periphery (Porph-O-Gn) and their metal complexes (M-[Porph-O-Gn]) are reported. The pyrene-containing Frechet-type dendrons up to the first generation were synthesized and further reacted with 5-phenol-10,15,20-triphenylporphyrin via an esterification reaction to afford the desired pyrene-labeled dendronized porphyrins. Later, these compounds were used as ligands to produce the corresponding complexes of Zn2+, Cu2+, Mg2+ and Mn3+. With the compounds in hand, the optical and photophysical properties of the dendritic metalloporphyrins were studied by absorption and fluorescence spectroscopy. The quantum yields, F?rster radius and efficiency of energy transfer were determined and discussed as a function of the structure and the donor-acceptor distances, finding an efficient energy transfer from the pyrene moiety to the metallated porphyrin core in each case.

A manganese porphyrin-α-cyclodextrin conjugate as an artificial enzyme for the catalytic epoxidation of polybutadiene

We describe a manganese porphyrin-α-cyclodextrin conjugate as a catalyst for the epoxidation of cis-polybutadiene with trans-epoxide preference, which is a reverse stereoselectivity as compared to normal porphyrin catalysts. A clamp-like mechanism is prop

A cost-efficient method for unsymmetrical Meso-aryl porphyrin synthesis using NaY zeolite as an inorganic acid catalyst

Herein we report the synthesis of unsymmetrical meso-aryl substituted porphyrins, using NaY zeolite as an inorganic acid catalyst. A comparative study between this method and the several synthetic strategies available in the literature was carried out. Our method presented a better, more cost-efficient rationale and displayed a significantly lower environmental impact. Furthermore, it was possible to verify the scalability of the process as well as the reutilization of the inorganic catalyst NaY (up to 6 times) without significant yield decrease. In addition, this method was applied to the synthesis of several other unsymmetrical porphyrins, from a low melting point porphyrin to mono-carboxylated halogenated unsymmetrical porphyrins, in yields higher than those found in the literature. Additionally, for the first time, two acetamide functionalized halogenated porphyrins were prepared in high yields. This methodology opens the way to the preparation of high yielding functionalized porphyrins, which can be easily immobilized for a variety of applications, either in catalysis or in biomedicine.

Magnetic Co(II) porphyrin nanospheres appending different substituent groups showing higher catalytic activities in cyclohexane

Magnetic polymer nanospheres immobilizing Co(II) porphyrins with different substituents were prepared and exhibited satisfying size, morphology and magnetic responsiveness. These core/shell structured nanospheres showed much higher catalytic activities in hydroxylating cyclohexane than the non-supported Co(II) porphyrin analogues. Moreover, these magnetic nanospheres could be easily recovered and reused for up to five times with maintaining their high catalytic efficiencies, and thus are good candidates for high-efficient, environmental-friendly catalysts.