238402-21-6

Basic information

• Product Name: 5,10,15-TRI(PENTAFLUOROPHENYL)CORROLE
• Synonyms: 5,10,15-TRI(PENTAFLUOROPHENYL)CORROLE
• CAS NO: 238402-21-6
• Molecular Formula: C37H9F15N4
• Molecular Weight: 794.47
• Product Categories: porphine (porphyrin) ligand
• Mol File: 238402-21-6.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5,10,15-TRI(PENTAFLUOROPHENYL)CORROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,10,15-TRI(PENTAFLUOROPHENYL)CORROLE(238402-21-6)
• EPA Substance Registry System: 5,10,15-TRI(PENTAFLUOROPHENYL)CORROLE(238402-21-6)

Safety Data

• Hazardous Substances Data: 238402-21-6(Hazardous Substances Data)

Usage

General Description

5,10,15-Tri(pentafluorophenyl)corrole is a chemical compound with a unique molecular structure consisting of a corrole core with three pentafluorophenyl groups attached at the 5th, 10th, and 15th positions. 5,10,15-Tri(pentafluorophenyl)corrole is often utilized in the field of organic chemistry for its ability to act as a versatile ligand in metal coordination chemistry. It is known for its strong electron-donating abilities and has been studied for its potential applications in catalysis, photodynamic therapy, and as a sensor for various metal ions. Additionally, its unique structure and properties make it a subject of interest in the development of new materials and pharmaceuticals. Overall, 5,10,15-Tri(pentafluorophenyl)corrole is a valuable compound with diverse potential applications in various scientific and industrial fields.

Upstream product

• 167482-91-9 5-(pentafluorophenyl)dipyrromethane 
• 925900-28-3 5,5'-((perfluorophenyl)methylene)bis(2-((perfluorophenyl)(1H-pyrrol-2-yl)methyl)-1H-pyrrole) 
• 109-97-7 pyrrole 
• 653-37-2 perfluorobenzaldehyde 
• 307930-64-9 (((perfluorophenyl)methylene)bis(1H-pyrrole-5,2-diyl))bis((perfluorophenyl)methanone) 
• 680575-57-9 1,9-bis(pentafluorophenylhydroxymethyl)-5-(pentafluorophenyl)dipyrromethane 

Downstream Products

• 1363155-16-1 [(Fe((O2N)2TF5PC))2(μ-oxo)] 
• 226922-75-4 5,10,15-tris(pentafluorophenyl)corrole iron(IV) chloride 
• 322641-60-1 5,10,15-tris-(pentafluorophenyl)corrolato gallium(III)(pyridine) 

Relevant articles and documents

Bismuth A3-corroles: Useful precursors for the development of meso- substituted free-base corroles

Systematic studies on regioselective functionalization reactions employing oxygen-, nitrogen-, and sulfur-containing nucleophiles with bismuth A3-corroles under the influence of a strong non-nucleophilic base are reported. In the case of the thiols and dithiols a high-yielding reaction procedure was established to obtain mono-, di-, and tri-functionalized corroles at room temperature within short reaction times. The described method offers a possibility to attach bifunctional linker molecules to the para-position of the meso-pentafluorophenyl groups at positions 5, 10, and 15 of the corrole macrocycle. The described reaction strategy may serve as a versatile protocol for the covalent binding of corroles to proteins or antibodies and may be utilized to attach corroles on, for example, gold or titanium surfaces to study surface-supported reactions.

Two-Step, One-Flask Synthesis of a Meso-Substituted Phlorin

A two-step, one-flask reaction of pyrrole with pentafluorobenzaldehyde and acetone was investigated to determine the potential for a streamlined synthesis of a phlorin and/or 5-isocorrole as an alternative to stepwise, dipyrromethanecarbinol routes. Analytical-scale reactions were performed examining the effect of reactant concentration, reactant ratio, acid catalyst (TFA or BF3·OEt2), concentration of acid catalyst, oxidant quantity, and reaction time on the distribution of phlorin and 5-isocorrole as well as three additional porphyrinoids (porphodimethene, porphyrin, and corrole). Phlorin was observed ubiquitously in yields up to 20-26%, whereas 5-isocorrole was not detected. Promising reaction conditions for the one-flask synthesis of the phlorin were performed on a preparative scale. The best reaction condition afforded the phlorin in an isolated yield of 20-21% (249-268 mg). Preliminary attempts to extend the methodology to the preparation of phlorins derived from other ketones resulted in a low yield of phlorin from acetophenone (5%) and no detectable phlorin from benzophenone. The discovery of reaction conditions for the two-step, one-flask synthesis of a phlorin provides easier access to this interesting compound, and provides encouragement for the further study of reactions of pyrrole with an aldehyde and a ketone.

Synthesis and characterization of cis-A2B-type meso-triaryl-substituted corroles

A practical synthesis of cis-A2B-type 5,10,15-triarylcorroles has been developed that involves [2+2]-type acid-catalyzed condensation of 5-aryldipyrromethane and 5-(pentafluorophenyl) dipyrromethane-1-carbinol and subsequent 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) induced oxidative cyclization. All the corroles thus synthesized were structurally well-characterized, and their optical and electrochemical properties were also studied.

The First Silicon(IV) Corrole Complexes: Synthesis, Structures, Properties, and Formation of a μ-Oxo Dimer

The first SiIV corrole complexes were synthesized in good yields by treatment of meso-triarylcorroles with tetrachlorosilane in 1,2-dichloroethane at 60 °C. The central silicon atom possesses a square-pyramidal coordination geometry with slight

Control of oligomerization and oxidation steps in the synthesis of tris(pentafluorophenyl)corrole

The mechanistic features of oligomerization and oxidative cyclization steps in the synthesis of tris(pentafluorophenyl)corrole (1) have been thoroughly studied. Separation of the intermediates by preparative HPLC and analysis by NMR spectroscopy and high