104322-39-6

Basic information

• Product Name: 5,10,15,20-tetrakis(2′,6′-difluorophenyl)porphyrin
• Synonyms: 5,10,15,20-tetrakis(2′,6′-difluorophenyl)porphyrin
• CAS NO: 104322-39-6
• Molecular Weight: 758.673
• Mol File: 104322-39-6.mol

Chemical Properties

• CAS DataBase Reference: 5,10,15,20-tetrakis(2′,6′-difluorophenyl)porphyrin(CAS DataBase Reference)
• NIST Chemistry Reference: 5,10,15,20-tetrakis(2′,6′-difluorophenyl)porphyrin(104322-39-6)
• EPA Substance Registry System: 5,10,15,20-tetrakis(2′,6′-difluorophenyl)porphyrin(104322-39-6)

Safety Data

• Hazardous Substances Data: 104322-39-6(Hazardous Substances Data)

Upstream product

• 109-97-7 pyrrole 
• 437-81-0 2,6-difluorobenzaldehyde 
• 213403-41-9 (2,6-difluorophenyl)di(pyrrol-2-yl)methane 
• 129715-35-1 3-(1,2-dicarbaclosododecaboran⁽¹²⁾-1-ylmethoxy)benzaldehyde 
• 871950-42-4 3-[3,5-di(o-carboranylmethoxy)benzyloxy]benzaldehyde 

Downstream Products

• 99038-25-2 [meso-5,10,15,20-tetrakis-(2,6-difluorophenyl)porhpyrinato]-iron(III) chloride 
• 117960-17-5 (5,10,15,20-tetrakis(2,6-difluorophenyl)porphinato)chromium(III) chloride 
• 119890-01-6 (5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrinato)Cu 
• 127552-21-0 tetrakis(2,6-difluorophenyl)porphinato ruthenium(II)(CO) 
• 119889-99-5 cobalt(II) 5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrin 
• 126581-10-0 [5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrinato]zinc(II) 

Relevant articles and documents

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.

Amphiphilic meso(sulfonate ester fluoroaryl)porphyrins: Refining the substituents of porphyrin derivatives for phototherapy and diagnostics

A set of amphiphilic fluorinated porphyrins appended with sulfonate ester groups were synthesized and fully characterized. The reaction proceeds efficiently, with high yields, with an improved methodology. Their potential use as imaging and phototherapeutic agents was assessed measuring relevant photophysical properties. It is shown that these porphyrins have good photostability, long triplet lifetimes (between 47 μs and 102 μs), high singlet oxygen quantum yields (0.74≤FD≤1.00), low fluorescence quantum yields (0.04) and sharp 19F NMR peaks. The data on the new meso(sulfonate ester fluoroaryl)porphyrins illustrate the potential of perfluorinated sulfonate esters to improve physical properties relevant for cancer imaging and photodynamic therapy.

Ecofriendly Porphyrin Synthesis by using Water under Microwave Irradiation

Water, under microwave irradiation and at a temperature of 473 K, reaches pressures above 16 bar, being capable to act as catalyst, without the use of organic solvents and oxidants, for meso-substituted porphyrin synthesis. Sustainability of the reaction is proved by E Factor=35 and EcoScale value of 50.5, the highest so far obtained for porphyrin synthesis. Methodology's wide versatility is clearly demonstrated by the good yields obtained for both aryl and alkyl substituted porphyrins. These reaction conditions represent a huge development, not only by using very high concentrations, minimizing organic solvent usage, but also by eradicating toxic expensive solvents and oxidants.

New hybrid materials based on halogenated metalloporphyrins for enhanced visible light photocatalysis

Photophysical and photochemical studies on 5,10,15,20-tetrakis(2,6-difluoro-5-N-methylsulfamylophenyl)porphyrin (F2PMet) and its cobalt(iii) and zinc(ii) complexes, including spectroscopic characteristics, photostability and photocatalytic activity, were carried out. The hybrid materials resulting from adsorption of these tetrapyrroles at the surface of titanium dioxide were prepared and examined in terms of their morphological, optical and functional properties applying absorption spectroscopy, scanning electron microscopy (SEM), photoelectrochemistry and photocatalytic tests. Our studies revealed that MF2PMet@TiO2 photocatalysts can be considered as the hybrid organic/inorganic photoactive materials enabling photodegradation of a synthetic opioid such as tramadol hydrochloride (TRML) and a model pollutant, 4-chlorophenol, in aqueous solution under visible light irradiation (λ > 400 nm). To elucidate mechanisms of photochemical processes, the photocatalytic activity of investigated metalloporphyrins was compared in homo- and heterogeneous systems. The results indicate that impregnation of TiO2 (P25) with functionalized porphyrins can improve its photoactivity. ZnF2PMet@TiO2 exhibited a superior photocatalytic performance towards TRML degradation. The role of singlet oxygen and hydroxyl radicals in photodegradation processes has been elucidated both for MF2PMet and MF2PMet@TiO2 systems.

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

Design Guidelines to Elongate Spin-Lattice Relaxation Times of Porphyrins with Large Triplet Electron Polarization

The spin-polarized triplet state generated by light irradiation has potential for applications such as triplet dynamic nuclear polarization (triplet-DNP). Recently, we have reported free-base porphyrins as versatile and biocompatible polarizing agents for triplet-DNP. However, the electron polarization of free-base porphyrins is not very high, and the dilemma is that the high polarization of metalloporphyrins is accompanied by a too short spin-lattice relaxation time to be used for triplet-DNP. We report here that the introduction of electron-withdrawing fluorine groups into Zn porphyrins enables a long enough spin-lattice relaxation time (>1 μs) while maintaining a high polarization (Px:Py:Pz = 0:0:1.0) at room temperature. Interestingly, the spin-lattice relaxation time of Zn porphyrin becomes much longer by introducing fluorine substituents, whereas the spin-lattice relaxation time of free-base porphyrin becomes shorter by the fluorine substitution. Theoretical calculations suggest that this is because the introduction of the electron-withdrawing fluorine substituents reduces the spin density on Zn atoms and weakens the spin-orbit interaction.

Bioinspired-metalloporphyrin magnetic nanocomposite as a reusable catalyst for synthesis of diastereomeric (-)-isopulegol epoxide: Anticancer activity against human osteosarcoma cells (MG-63)

In the present study, we developed a green epoxidation approach for the synthesis of the diastereomers of (-)-isopulegol benzyl ether epoxide using molecular oxygen as the oxidant and a hybrid manganese(III)-porphyrin magnetic reusable nanocomposite as th

Improved syntheses of 5,10,15,20-tetrakisaryl- and tetrakisalkylporphyrins

Three significant modifications to existing methods for the preparation of the important 5,10,15,20-tetrakisarylporphyrins have improved isolated yields, simplified work-up and made large-scale synthesis feasible. Two tetrakisalkylporphyrins were also produced. A two-stage approach using hydrogen peroxide in acetic acid as second stage oxidant gave good yields but for ease of isolation and convenience in working on a large scale, the one-pot approach is preferred. No one method appears to be suitable for all such tetrakisarylporphyrins and, for best yields, the method of preparation needs to be chosen carefully. Application of statistical optimisation techniques (factorial two design and simplex operation) led to considerably enhanced yields for the one-pot method. For one of the two-stage modifications, significant amounts of chlorins were observed, sometimes of such magnitude as to make it suitable as a method for their preparation.

Rate-Limiting Step of Epoxidation Reaction of the Oxoiron(IV) Porphyrin π-Cation Radical Complex: Electron Transfer Coupled Bond Formation Mechanism

Epoxidation reactions catalyzed by high-valent metal-oxo species are key reactions in various biological and chemical processes. Because the redox potentials of alkenes are higher than those of most high-valent metal-oxo species, the electron transfer (ET

Nitric Oxide Dioxygenase Activity of a Nitrosyl Complex of Cobalt(II) Porphyrinate in the Presence of Hydrogen Peroxide via Putative Peroxynitrite Intermediate

The reaction of a cobalt porphyrin complex, [(F8TPP)Co], 1 {F8TPP = 5,10,15,20-tetrakis(2,6-difluorophenyl)porphyrinate dianion} in dichloromethane with nitric oxide (NO) led to the nitrosyl complex, [(F8TPP)Co(NO)], 2. Spectroscopic studies and structural characterization revealed it as a bent nitrosyl of {CoNO}8 description. It was stable in the presence of dioxygen. However, it reacts with H2O2 in acetonitrile (or THF) solution at -40 °C (or -80 °C) to result in the corresponding Co(III)-nitrate complex, [(F8TPP)Co(NO3)], 3. The reaction presumably proceeds via the formation of a Co-peroxynitrite intermediate. X-Band electron paramagnetic resonance and electrospray ionization-mass spectroscopic studies suggest the intermediate formation of the [(porphyrin)Co(III)-O?] radical, which in turn supports the generation of the corresponding Co(IV)-oxo species during the reaction. This is in accord with the homolytic cleavage of the O-O bond in heme-peroxynitrite proposed in the nitric oxide dioxygenases activity. In addition, the characteristic peroxynitrite-induced phenol ring reaction was also observed.