63160-31-6

Upstream product

• 917-23-7 5,15,10,20-tetraphenylporphyrin 
• 124-41-4 sodium methylate 
• 14172-91-9 (tetraphenylporphyrin)copper(II) 

Downstream Products

• 574735-14-1 (2,3-dioxo-5,10,15,20-tetrakisphenylchlorinato)zinc(II) 
• 1412456-47-3 [2-amino-3-nitro-5,10,15,20-tetraphenylporphyrinato]zinc(II) 
• 71435-57-9 (2-nitro-5,10,15,20-tetraphenylporphyrinato)zinc(II) 
• 132345-39-2 [2-amino-5,10,15,20-tetraphenylporphyrinato]copper (II) 
• 1415029-88-7 (2-amino-5,10,15,20-tetraphenylporphyrinato)zinc(II) 

Relevant academic research and scientific papers

Synthetic access to new porphyrinoids from 2-nitro-5,10,15,20-tetraphenylporphyrin and an arylacetonitrile

Abstract: In this work, the reactivity of 2-nitro-5,10,15,20-tetraphenylporphyrin with 2-(4-nitrophenyl)acetonitrile in the presence of KOH as base was studied. Under these conditions, three new compounds were isolated: a β-di-substituted derivative, as the major compound, accompanied by two minor products, a π-extended and a β-isoxazoline-fused derivative, all in acceptable yields. A preliminary study was also performed in the presence of K2CO3. It allowed the isolation of a cyclopropyl-annulated chlorin in very good yield. All the obtained products were photochemically and photophysically characterized, some of them showing promising properties to be used as photosensitizers in photodynamic processes. Graphical abstract: [Figure not available: see fulltext.].

Beta-(2,3-dihydro-naphthyl[1,2,e]-m-oxazinyl) tetraphenylporphyrin, and preparation method and application thereof

The invention discloses beta-(2,3-dihydro-naphthyl[1,2,e]-m-oxazinyl)tetraphenylporphyrin of which the structural general formula is disclosed as Formula (I) or Formula (II), and a preparation method and application thereof. The preparation method comprises the following steps: 1) preparing 5,10,15,20-tetraphenyl porphyrin from pyrrole and benzaldehyde, carrying out coordination with copper to obtain 5,10,15,20-tetraphenyl copper porphyrins, carrying out regioselective nitration to obtain beta-nitro-substituted-5,10,15,20-tetraphenyl copper porphyrins, carrying out decoppering and reduction to obtain beta-amino-substituted-5,10,15,20-tetraphenyl porphyrins, and reacting with acetate to obtain beta-amino-substituted-tetraphenyl metalloporphyrins (beta-NH2-MTPP); 2) carrying out condensation reaction on the beta-NH2-MTPP, formaldehyde and 2-naphthol, separating the product by column chromatography to obtain a beta-(2,3-dihydro-1H-naphthyl[1,2,e]-m-oxazinyl)-substituted tetraphenyl porphyrin metal complex; and decoppering to obtain the beta-(2,3-dihydro-naphthyl[1,2,e]-m-oxazinyl)tetraphenylporphyrin. The compounds can be used for preparing photodynamic-therapy photosensitizers and antineoplastic drugs with small toxic and side effects and high activity.

Synthesis and properties of bis-porphyrin molecular tweezers: Effects of spacer flexibility on binding and supramolecular chirogenesis

Ditopic binding of various dinitrogen compounds to three bisporphyrin molecular tweezers with spacers of varying conformational rigidity, incorporating the planar enediyne (1), the helical stiff stilbene (2), or the semi-rigid glycoluril motif fused to the porphyrins (3), are compared. Binding constants Ka = 104-106 M-1 reveal subtle differences between these tweezers, that are discussed in terms of porphyrin dislocation modes. Exciton coupled circular dichroism (ECCD) of complexes with chiral dinitrogen guests provides experimental evidence for the conformational properties of the tweezers. The results are further supported and rationalized by conformational analysis.

β-Pyrazino-fused tetrarylporphyrins

A novel method for the preparation of β-fused porphyrin dyads was developed that exploits a one-pot reaction of 2,3-diaminoporphyrins with diethyl oxalate. This approach provides good yields of the zinc β-fused dyad and the corresponding free-base, openin

Reaction of metallo-2-nitro-5,10,15,20-tetraphenylporphyrins with oxyanions. Temperature-dependent competition between nucleophilic addition and single-electron transfer processes

The outcome of the reaction of metallo-2-nitro-5,10,15,20-tetraphenylporphyrins with oxyanions is dependent both on the nature of the coordinated metal ion and on the reaction temperature, Metallo-2-nitro-5,10,15,20-tetraphenylporphyrins with relatively electronegative chelated metal ions (CuII, NiII and FeIIICl) react with methoxideionin N,N-dimethylformamide to afford mainly the corresponding metallated 2-methoxy-3-nitroporphyrins and 2,2-dimethoxy-3-nitro-2,3-dihydroporphyrins. The zincII chelate 7 is unreactive towards methoxide under identical conditions. When the room temperature reaction of (2-nitro-5,10,15,20-tetraphenylporphyrinato)nickel(II) 5 with methoxide is quenched with water after 1 min, the trans-(2-methoxy-3-nitro-2,3-dihydroporphyrinato)nickel(II) 14 is obtained. Inclusion of nitrobenzene in the reaction of the copper(II) chelate 4 with methoxide is beneficial and results in the formation of the 2,2-dimethoxy-3-nitro-2,3-dihydroporphyrin 8 in 90% yield. Reaction of 4 with benzyl oxide ion gives analogous products but in lower yield, while the major product from reaction of 4 with hydroxide ion is the 2-hydroxy-3-nitroporphyrin 16. At elevated temperatures the nature of the reaction of the copper(II) chelate 4 with methoxide changed to afford the corresponding copper(II) 2-alkoxyporphyrin 10 and the denitrated parent porphyrin 20; the later compounds arise from radical reactions. A mechanistic rationale for the processes involved in these temperature-dependent reactions is presented. The ease with which these reactions occur is a consequence of the fact that all the reaction intermediates are able to retain macrocyclic aromaticity.

Rections of Porphyrins with Nitronium Tetrafluoroborate in Pyridine

Octaethylporphyrin reacts with nitronium tetrafluoroborate in pyridine at 80 deg C to afford the meso-nitroporphyrin in 31percent yield after 6 h, whereas the zinc complex reacts very rapidly at 20 deg C to afford 63percent of the meso-nitroporphyrin after work-up. meso-Tetraphenylporphyrin, however, only reacted slowly with nitronium tetrafluoroborate in pyridine at rather higher temperatures in a sealed tube to afford the β-pyridinium salt of the porphyrin as the major product; again when the zinc complex of tetraphenylporphyrin was used the β-pyridinium salt was formed in 85percent yield in a few minutes at 20 deg C.Brief treatment of the tetraphenylporphyrin pyridinium salt with alkali afforded a ring-opened glutaconaldehyde derivative of the β-aminoporphyrin, analogous to the well-known Zincke's compounds which can be obtained from N-arylpyridines with alkali.The structures of both the ring-opened products from the pyridinium porphyrin and from N-(2,4-dinitrophenyl)pyridinium chloride, were assigned by highfield n.m.r. spectroscopy, including decoupling and n.O.e. difference measurements.