37083-37-7

Usage

Uses

Used in Photodynamic Therapy (PDT):
5,10,15,20-TETRAKIS(2,6-DICHLOROPHENYL)PORPHINE is used as a photosensitizer for Photodynamic Therapy (PDT) due to its ability to absorb light and generate reactive oxygen species, which can be employed to target and destroy cancer cells.
Used in Coordination Complexes:
In the field of coordination chemistry, 5,10,15,20-TETRAKIS(2,6-DICHLOROPHENYL)PORPHINE is used to create coordination complexes with metals such as ruthenium and palladium. These complexes exhibit unique electronic, optical, and catalytic properties, making them valuable in various applications, including catalysis and molecular electronics.
Used in Environmental Applications:
5,10,15,20-TETRAKIS(2,6-DICHLOROPHENYL)PORPHINE is used as an environmentally friendly photocatalyst for the degradation of pesticides in soils. Its photocatalytic properties enable the conversion of sunlight into chemical energy, which can be utilized to break down harmful pollutants, contributing to environmental remediation efforts.
Used in Solar Energy Conversion:
In the renewable energy sector, 5,10,15,20-TETRAKIS(2,6-DICHLOROPHENYL)PORPHINE is used as a component in dye-sensitized solar cells (DSSCs). Its light-harvesting capabilities and ability to inject electrons into the conduction band of semiconductors make it a promising candidate for improving the efficiency of solar energy conversion devices.
Used in Analytical Chemistry:
5,10,15,20-TETRAKIS(2,6-DICHLOROPHENYL)PORPHINE is employed as a selective and sensitive probe for the detection of various metal ions and other analytes in analytical chemistry. Its unique optical properties allow for the development of novel sensors and analytical methods, enhancing the detection and quantification of target analytes in complex samples.

InChI:InChI=1/C44H22Cl8N4/c45-21-5-1-6-22(46)37(21)41-29-13-15-31(53-29)42(38-23(47)7-2-8-24(38)48)33-17-19-35(55-33)44(40-27(51)11-4-12-28(40)52)36-20-18-34(56-36)43(32-16-14-30(41)54-32)39-25(49)9-3-10-26(39)50/h1-20,53,56H/b41-29+,41-30+,42-31+,42-33+,43-32+,43-34+,44-35+,44-36+

Upstream product

• 109-97-7 pyrrole 
• 29866-54-4 2-chloro-6-methoxybenzaldehyde 
• 83-38-5 2,6-dichlorobenzaldehyde 
• 6361-22-4 2-chloro-6-nitrobenzaldehyde 
• 5866-97-7 2,6-dichloro-3-nitrobenzaldehyde 
• 6505-37-9 2,6-dichloro-3-methoxybenzaldehyde 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 1571-08-0 methyl 4-formylbenzoate 
• 653-37-2 perfluorobenzaldehyde 
• 194796-34-4 (2,6-dichlorophenyl)dipyrrol-2-ylmethane 
• 100-52-7 benzaldehyde 
• 6575-24-2 2-(2,6-dichlorophenyl)acetic acid 

Downstream Products

• 120644-24-8 5,10,15,20-tetrakis(2',6'-dichloro-3'-sulfonatophenyl)porphyrin 
• 135685-21-1 Cu(5,10,15,20-tetra(2',6'-dichlorophenyl)porphyrinate) 
• 91042-27-2 5,10,15,20-tetra(2',6'-dichlorophenyl)porphyrinatoiron(III) chloride 
• 127390-19-6 [Ru(2,6-Cl₂tpp)CO] 
• 127390-19-6 carbonyl ruthenium(II) 5,10,15,20-tetra(2,6-dichlorophenyl)porphyrin 
• 91463-17-1 chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III) 
• 120882-91-9 [5,10,15,20-tetrakis(2,6-dichlorophenyl)porphinato]cobalt(II) 

Relevant academic research and scientific papers

A nonionic porphyrin as a noninterfering DNA antibacterial agent

The increasing interest in clinical bacterial photodynamic inactivation has led to the search for photosensitizers with higher bactericidal efficiency and less side effects on the surrounding tissues. We present a novel nonionic porphyrin, the 5,10,15-tri

Improved protocols for the synthesis and halogenation of sterically hindered metalloporphyrins

Improved procedures are described for the synthesis of meso-tetrakis(2,6-dichlorophenyl)porphyrin and for subsequent perhalogenation of the porphyrin ring.

Efficient oxidation of cycloalkanes with simultaneously increased conversion and selectivity using O2 catalyzed by metalloporphyrins and boosted by Zn(AcO)2: A practical strategy to inhibit the formation of aliphatic diacids

The direct sources of aliphatic acids in cycloalkanes oxidation were investigated, and a strategy to suppress the formation of aliphatic acids was adopted through enhancing the catalytic transformation of oxidation intermediates cycloalkyl hydroperoxides to cycloalkanols by Zn(II) and delaying the emergence of cycloalkanones. Benefitted from the delayed formation of cycloalkanones and suppressed non-selective thermal decomposition of cycloalkyl hydroperoxides, the conversion of cycloalkanes and selectivity towards cycloalkanols and cycloalkanones were increased simultaneously with satisfying tolerance to both of metalloporphyrins and substrates. For cyclohexane, the selectivity towards KA-oil was increased from 80.1% to 96.9% meanwhile the conversion was increased from 3.83 % to 6.53 %, a very competitive conversion level with higher selectivity compared with current industrial process. This protocol is not only a valuable strategy to overcome the problems of low conversion and low selectivity lying in front of current cyclohexane oxidation in industry, but also an important reference to other alkanes oxidation.

Synthesis of meso-substituted corroles and porphyrins using iodine as a catalyst

Abstract: Different types of corroles and porphyrins are synthesized from substituted aldehydes and pyrrole. The current synthetic method involves iodine as catalyst and proceeds at room temperature itself. By varying the amounts of reactants (i.e., pyrrole and aldehydes), the corrole and porphyrins were obtained in good to excellent yields. These products were characterized by 1H-NMR, UV-visible, and HRMS techniques. The reaction approach utilizes the readily available pyrrole and substituted aldehydes as starting materials and makes this reaction highly attractive in diversity-oriented synthesis. Graphic abstract: Different types of porphyrins and corroles are synthesized from substituted aldehydes and pyrrole using iodine as a catalyst and the reaction proceeds at room temperature itself. By varying the amount of reactants (i.e. pyrrole and aldehydes), the porphyrins and corroles are obtained in good to excellent yields.[Figure not available: see fulltext.]

Selective Solvent-Free and Additive-Free Oxidation of Primary Benzylic C–H Bonds with O2 Catalyzed by the Combination of Metalloporphyrin with N-Hydroxyphthalimide

Abstract: A protocol for solvent-free and additive-free oxidation of primary benzylic C–H bonds with O2 was presented through adjusting the combination of metalloporphyrins and NHPI as binary catalysts to overcome the deficiencies encountered in current oxidation systems. The effects of reaction temperature, porphyrin structure, central metal, catalyst loading and O2 pressure were investigated systematically. For the optimized combination of T(2-OCH3)PPCo and NHPI, all the primary benzylic C–H bonds could be functionalized efficiently and selectively at 120 °C and 1.0?MPa O2 with aromatic acids as the primary products. The selectivity towards aromatic acids could reach up to 70–95% in the conversion of more than 30% for most of the substrates possessing primary benzylic C–H bonds in the metalloporphyrin loading of 0.012% (mol/mol). And the superior performance of T(2-OCH3)PPCo among the metalloporphyrins investigated was mainly attributed to its high efficiency in charge transfer and fewer positive charges around central metal Co (II) which favored the adduction of O2 to cobalt (II) forming the high-valence metal-oxo complex followed by the production of phthalimide N-oxyl radical (PINO) and the initiation of the catalytic oxidation cycle. This work would provide not only an efficient protocol in utilization of hydrocarbons containing primary benzylic C–H bonds, but also a significant reference in the construction of more efficient C–H bonds oxidation systems. Graphic Abstract: The solvent-free and additive-free oxidation of primary benzylic C–H bonds with O2 was presented through adjusting the combination of metalloporphyrins and NHPI as binary catalysts, and the highest selectivity towards aromatic acid reached up to 95.1% with the conversion of 88.5% in the optimized combination of T(2-OCH3)PPCo and NHPI.[Figure not available: see fulltext.].

Biologically Inspired and Magnetically Recoverable Copper Porphyrinic Catalysts: A Greener Approach for Oxidation of Hydrocarbons with Molecular Oxygen

An efficient synthetic method for magnetically recoverable hybrid copper porphyrinic nanomaterials is reported. These functionalized magnetic materials prove to be efficient bioinspired oxidation catalysts of olefins and thiols, using molecular oxygen as oxidant, in total absence of reductants and solvents, with the highest TON (turnover number) yet achieved for this reaction (≈200 000). A comparative study between homogeneous and heterogeneous oxidation of cyclohexene is discussed, revealing the heterogeneous system to be the most promising concerning stability and reusability of the catalysts. The full characterization of the magnetic hybrid porphyrinic nanomaterials, by transmission electron microscopy, flame atomic absorption spectrometry, thermogravimetry, N2 sorption, and infrared spectroscopy, is also described.

Effects of porphyrin deformation on the 13 C and 1H NMR chemical shifts in high-spin five-and six-coordinate manganese(III) porphyrin complexes

As an extension of our study to reveal the effect of porphyrin deformation on the 13C and 1H NMR chemical shifts, both five-and six-coordinate high-spin (S = 2) Mn(III) complexes such as Mn(Por)Cl and [Mn(Por)(CD3OD)2]Cl h

Halogenated meso-phenyl Mn(III) porphyrins as highly efficient catalysts for the synthesis of polycarbonates and cyclic carbonates using carbon dioxide and epoxides

Introduction of halogen electron withdrawing atoms (chloro and fluoro) in the ortho position of the aryl groups of meso-tetraphenylporphyrin manganese(III) complexes increased their activity as catalysts in the reaction of carbon dioxide with epoxides, wh

Sulfonated graphenes catalyzed synthesis of expanded porphyrins and their supramolecular interactions with pristine graphene

A newer synthesis of sulfonic acid functionalized graphenes have been developed, which have been characterized, examined as heterogeneous solid acid carbocatalyst in the synthesis of selected expanded porphyrins in different reaction conditions. This envi

Biomimetic oxidation of indole by Mn(III)porphyrins

The oxidation of indole under biomimetic conditions in the presence of Mn(III)porphyrins and using hydrogen peroxide as a green oxidant is described. The metalloporphyrins act as chemical models of the enzymes involved in the natural and biocatalytic oxidation of indole to afford indigo dye, but leading to simplified systems, with significantly lower cost requirements, as higher indole conversions and easier product isolation are obtained. The distribution of the products that include 2-oxoindole, isatin, 2,2′-bis(3′- indolyl)-3-oxoindole and the indigoid pigments, indigo and indirrubin, was found to be dependent on the reaction time, the amount of oxidant and the electronic characteristics of the metalloporphyrin catalyst. Upon 30 min of reaction time, 85% of indole conversion was achieved. The best conditions for pigment formation and isolation included the separation of the initially formed 3-indoxyl from the oxidizing reaction mixture, followed by heating to obtain the air oxidative dimerization.