22112-79-4

Usage

Uses

Used in Photodynamic Therapy:
5,10,15,20-tetra(3-hydroxyphenyl)porphyrin is used as a photosensitizer in photodynamic therapy for cancer treatment. It can be activated by light to generate reactive oxygen species, which can selectively destroy cancer cells while minimizing damage to surrounding healthy tissue.
Used in Sensor Development:
In the materials science field, 5,10,15,20-tetra(3-hydroxyphenyl)porphyrin is used as a component in the development of new materials for sensors. Its unique optical and electronic properties make it suitable for detecting various analytes, including gases, ions, and biomolecules.
Used in Solar Cell Manufacturing:
5,10,15,20-tetra(3-hydroxyphenyl)porphyrin is utilized as a component in the manufacturing of solar cells. Its light-absorbing properties and ability to facilitate charge transfer make it a promising candidate for improving the efficiency and performance of solar energy conversion devices.
Used in Electronic Device Development:
This porphyrin compound is also used in the development of new materials for electronic devices, such as organic light-emitting diodes (OLEDs) and field-effect transistors (FETs). Its electronic properties and compatibility with other materials make it a valuable component in creating advanced electronic devices with improved performance and functionality.
Used in Catalyst Design:
5,10,15,20-tetra(3-hydroxyphenyl)porphyrin is employed as a catalyst or catalyst precursor in various chemical reactions. Its ability to bind and activate substrates, as well as facilitate electron transfer, makes it a versatile and efficient catalyst for a wide range of applications in the chemical industry.

Upstream product

• 63057-26-1 5,10,15,20-mesotetrakis(3-aminophenyl)-21H,23H-porphyrine 
• 34231-78-2 3-formylphenyl acetate 
• 109-97-7 pyrrole 
• 100-83-4 meta-hydroxybenzaldehyde 
• 591-31-1 3-methoxy-benzaldehyde 

Downstream Products

• 96344-57-9 tetra(m-butoxyphenyl)porphin 
• 29114-93-0 meso-tetra(m-methoxyphenyl)porphyrin 
• 541-59-3 maleiimide 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 102498-02-2 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrinatozinc(II) 
• 591751-85-8 meso-tetra(3-hydroxyphenyl)porphyrin-Cu(II) 
• 1207995-76-3 [5,10,15,20-tetra(3-hydroxyphenyl)]porphyrinato manganese (III) chloride 
• 122341-38-2 temoporfin 

Relevant academic research and scientific papers

Development of antimicrobial laser-induced photodynamic therapy based on ethylcellulose/chitosan nanocomposite with 5,10,15,20-tetrakis(M-hydroxyphenyl)porphyrin

The development of new antimicrobial strategies that act more efficiently than traditional antibiotics is becoming a necessity to combat multidrug-resistant pathogens. Here we report the effi-cacy of laser-light-irradiated 5,10,15,20-tetrakis(m-hydroxyphenyl)porphyrin (mTHPP) loaded onto an ethylcellulose (EC)/chitosan (Chs) nanocomposite in eradicating multi-drug resistant Pseudomonas aeruginosa, Staphylococcus aureus, and Candida albicans. Surface loading of the ethylcelllose/chitosan composite with mTHPP was carried out and the resulting nanocomposite was fully characterized. The results indicate that the prepared nanocomposite incorporates mTHPP inside, and that the composite acquired an overall positive charge. The incorporation of mTHPP into the nanocomposite enhanced the photo-and thermal stability. Different laser wavelengths (458; 476; 488; 515; 635 nm), powers (5–70 mW), and exposure times (15–45 min) were investigated in the antimicrobial pho-todynamic therapy (aPDT) experiments, with the best inhibition observed using 635 nm with the mTHPP EC/Chs nanocomposite for C. albicans (59 ± 0.21%), P. aeruginosa (71.7 ± 1.72%), and S. aureus (74.2 ± 1.26%) with illumination of only 15 min. Utilization of higher doses (70 mW) for longer periods achieved more eradication of microbial growth.

The synthesis of new potential photosensitizers

Abstract Several new derivatives of tetrakis(hydroxyphenyl)porphyrin were synthesized and their physicochemical data were established. These data were further assessed in terms of the synthesized compounds' usefulness as potential photosensitizers in anticancer photodynamic therapy. Absorption and fluorescence spectra, as well as triplet state lifetime were determined along with the compounds' stability and capacity to generate singlet oxygen. They obtained were compared to the corresponding data pertaining to a well-known and clinically admitted photosensitizing drug (Foscan).

Effects of substituents on the photophysical properties of symmetrical porphyrins

Porphyrin compounds having groups that mimic the phenolic moiety of m- and p-isomers of 5,10,15,20-tetrakis(hydroxyphenyl) porphyrin (THPP) have been synthesized along with 5,10,15,20-tetrakis(heteroaryl) porphyrins bearing 2-thienyl and 5-thiazolyl groups. Absorption and fluorescence spectroscopy, including fluorescence lifetime (τf) and quantum yield (Φf) measurements, were employed to characterize the singlet excited state of all compounds, using 5,10,15,20-tetraphenylporphyrin (H 2TPP) as a standard (Φf = 0.12 in DMF). The generation of singlet oxygen by each porphyrin photosensitizer was measured as the singlet oxygen quantum yield (ΦΔ), using H2TPP as a standard (ΦΔ = 0.64 in DMF). Partition coefficients were determined using 2-octanol as the organic phase and PBS solution as the aqueous phase. Fluorescence quantum yields ranged from 0.01 to 0.18 for all compounds, with heteroaryl porphyrins having the lowest values. Singlet oxygen quantum yields ranged from 0.40 to 0.65, with heteroaryl porphyrins having the highest values, showing them to be better sensitizers than m- and p-THPP. Log P values were all >1 showing higher solubility in the 2-octanol layer.

Synthesis, photophysical properties and DNA-Binding Studies of p-Hydroxy and m-Hydroxy Amphiphilic Porphyrins

Three p-hydroxy and m-hydroxy amphiphilic porphyrins had been synthesized and fully characterized by 1H NMR, IR and FAB-MS. Their photophysical properties were also determined. Furthermore, the UV-visible absorption and fluorescence emission titration exp

Synthesis and biological distribution study of a new carbon-11 labeled porphyrin for PET imaging. Photochemical and biological characterization of the non-labeled porphyrin

Ideal reaction conditions were found to promote the "cold" monomethylation of 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin with CH3I, at minute time scale, in the presence of base. The photophysical characterization, cellular uptake and dark cytotoxicity of the resulting monomethylated porphyrin were appraised. Moreover, the syntheses of the corresponding labeled porphyrin, using short-lived carbon-11, prepared in the automated radiolabeling system were efficiently performed. The purification of the labeled product was achieved via preparative HPLC with high radiochemical purity and specific radioactivity. Preliminary studies on the biodistribution of 5,10,15-tris(3-hydroxyphenyl)-20-(3-[11C]methoxyphenyl)porphyrin carried out in a BALB/C normal mouse, using PET imaging, showed that the liver is the main pathway for excretion.

Porphyrin n-pincer pd(Ii)-complexes in water: A base-free and nature-inspired protocol for the oxidative self-coupling of potassium aryltrifluoroborates in open-air

Metalloporphyrins (and porphyrins) are well known as pigments of life in nature, since representatives of this group include chlorophylls (Mg-porphyrins) and heme (Fe-porphyrins). Hence, the construction of chemistry based on these substances can be based on the imitation of biological systems. Inspired by nature, in this article we present the preparation of five different porphyrin, meso-tetraphenylporphyrin (TPP), meso-tetra(p-anisyl)porphyrin (TpAP), tetra-sodium meso-tetra(p-sulfonatophenyl)porphyrin (TSTpSPP), meso-tetra(m-hydroxyphenyl)porphyrin (TmHPP), and meso-tetra(m-carboxyphenyl)porphyrin (TmCPP) as well as their N-pincer Pd(II)-complexes such as Pd(II)-meso-tetraphenylporphyrin (PdTPP), Pd(II)-meso-tetra(p-anisyl)porphyrin (PdTpAP), Pd(II)-tetrasodium meso-tetra(p-sulfonatophenyl)porphyrin (PdTSTpSPP), Pd(II)-meso-tetra(m-hydroxyphenyl)porphyrin (PdTmHPP), and Pd(II)-meso-tetra(m-carboxyphenyl)porphyrin (PdTmCPP). These porphyrin N-pincer Pd(II)-complexes were studied and found to be effective in the base-free self-coupling reactions of potassium aryltrifluoroborates (PATFBs) in water at ambient conditions. The catalysts and the products (symmetrical biaryls) were characterized using their spectral data. The high yields of the biaryls, the bio-mimicking conditions, good substrate feasibility, evading the use of base, easy preparation and handling of catalysts, and the application of aqueous media, all make this protocol very attractive from a sustainability and cost-effective standpoint.

New approach for the synthesis, docking of new porphyrins and their antitumor activity

A new methodology for the synthesis of a new series of mesotetrakis[aryl]-21H,23H-porphyrin derivatives 5a-5d, 6a-6c, 7 and 8 is presented. Structures of new compounds were established based on both elemental and spectral data. Cytotoxicity activity of the newly synthesized compounds was investigated against two human cell lines MCF-7 and HepG2. Molecular docking was performed to investigate the binding between the most active porphyrin derivatives and Bcl-2 molecular biomarkers in HepG2 cells.

Synthesis of amphiphilic meso -tetrasubstituted porphyrin-L-amino acid and -heterocyclic conjugates based on m -THPP

Two series of amphiphilic meso-tetrasubstituted porphyrin conjugates based on 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin (m-THPP) covalently linked to L-amino acids and heterocycles were synthesized efficiently in the context of a program targeting new photosensitizers for PDT. 5,10,15-Tris(3-hydroxyphenyl)-20-(3-oxyacetic acid)phenyl]porphyrin and the respective trihexyl ether derivatives were conjugated with polar and non-polar natural L-amino acids such as glycine, L-proline, and L-tyrosine via an amide bond linker using N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uroniumhexafluorophosphate in diisopropylethylamine (HBTU/DIPEA). m-THPP was also conjugated with heterocyclic systems such as indole 3-acetic acid, 4-methylthiazole-5-carboxylic acid, and thiophene-2-carboxylic acid via ester linker using N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride in N-hydroxysuccinamide or 1-hydroxybenzotriazole (EDCI, NHS or HOBt). The members of the two series were obtained in good yields and characterized by UV-vis, HRMS MALDI-TOF, 1H NMR and 13C NMR spectroscopy.

A four-phenyl porphine production method (by machine translation)

The invention discloses a production method for tetraphenyl porphin. The production method includes the steps that 1, pyrrole and aromatic aldehyde are prepared into a mixed solution for standby application; 2, solvent is added into a polymerization reactor, the pressure of the polymerization reactor is maintained at 1-5 atm, the mixed solution obtained in the step 1 starts to be dripped to start a polymerization reaction, after the reaction is finished, reaction products are cooled to normal temperature, and filter liquor and a filter cake are obtained through filtration; 3, the filter cake obtained in the step 2 and propionic acid are added into an oxidation reactor, oxygen-containing gas is introduced to carry out an oxidation reaction, cooling is carried out after oxidation is finished, a solid and filter liquor are obtained through filtration, and the solid is washed and dried to obtain the tetraphenyl porphin. The production method has the advantages of being high in yield, safe and environmentally friendly, separation and purification are easy, and the production quality is stable.

A four-phenyl porphine preparation method

The invention discloses a preparation method of meso-tetraphenylchlorin. The preparation method comprises the steps that 1, a mixed solution of pyrrole and aromatic aldehyde is prepared for standby; 2, a solvent is added into a polymerization reactor, nitrogen displacement is conducted till the concentration of tail oxygen is lower than 1%, the solvent is heated to backflow, the mixed solution obtained in the first step starts to be dropwise added, a reaction is started, after the mixed solution is dropwise added completely, the reaction is continuously conducted for 0.05 h to 0.5 h, and then the reaction is stopped; 3, oxygen-containing gas with the oxygen volume fraction ranging from 5% to 100% is fed into the polymerization reactor for oxidation, cooling is conducted after the oxidation is completed, filtration is conducted to obtain a filter cake and filtrate, and a product is obtained after the filter cake is washed and dried. The preparation method of the meso-tetraphenylchlorin has the advantages that the yield is high, safety and environmental protection are achieved, separation and purification are easy, and the product quality is stable.