<i>meso</i>‐Ester Corroles

Canard, Gabriel; Gao, Di; D’Aléo, Anthony; Giorgi, Michel; Dang, Florian-Xuan; Balaban, Teodor Silviu

doi:10.1002/chem.201406369

Cited by 26 publications

(25 citation statements)

References 124 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…But the high price of that aldehyde, the low yield (1 %) of the produced corrole, and its surprisingly low solubility were discouraging regarding further development. Quite recently, Balaban and co‐workers reported the synthesis of meso ‐triestercorrole ( 1 ‐H 3 , Scheme ), the gallium and manganese complexes of which displayed cellular anticancer activity, while the corresponding phosphorous derivative was investigated for its electrochemical and photophysical properties . A more appealing target would be 5,10,15‐tris(trifluoromethyl) corrole (TFC‐H 3 , Scheme ), which we failed producing at that time and even in later studies.…”

Section: Methodssupporting

confidence: 74%

One‐Pot Synthesis of Contracted and Expanded Porphyrins with meso‐CF₃ Groups

et al. 2017

View full text Add to dashboard Cite

Corrole and sapphyrin with the smallest meso-substituents reported so far were prepared in a one-pot synthesis that relies on a non-aldehydic precursor for introducing CF groups. The substantial amounts of products obtained by this facile pathway allowed for the full characterization of 5,10,15-tris(trifluoromethyl)corrole, the access to a variety of stable chelates thereof and investigations that disclose the unique structural and chemical properties induced by the CF substituents. The novel 5,10,15,20-tetra(trifluoromethyl)sapphyrin undergoes only single protonation, which according to its crystal structure is stabilized by favorable non-bonding F/H interaction between the meso-CF and the inverted pyrrolic NH.

show abstract

Section: Methodssupporting

confidence: 74%

One‐Pot Synthesis of Contracted and Expanded Porphyrins with meso‐CF₃ Groups

et al. 2017

View full text Add to dashboard Cite

show abstract

“…This behavior is in agreement with published results that underline the strong contribution of groups at the corrole meso positions 5 and 15 to the electronic spectrum compared to the smaller contribution from groups at the 10 position of the macrocycle. 40,48 To further investigate the scope of the synthetic route for obtaining triferrocenylcorroles, we attempted to prepare the cobalt and nickel derivatives of TFcCorrH 3 . In the case of TFcCorrCo(PPh 3 ), the mixture containing TFcCorrH 3 was dissolved in CHCl 3 /CH 3 OH along with an excess of Co(AcO) 2 and PPh 3 and stirred to reflux, while monitoring the course of the reaction by UV−visible spectroscopy and TLC analysis.…”

Section: Inorganic Chemistrymentioning

confidence: 99%

5,10,15-Triferrocenylcorrole Complexes

et al. 2015

View full text Add to dashboard Cite

Complexes of 5,10,15-triferrocenylcorrole were synthesized from the crude free-base corrole product obtained by the reaction of ferrocenyl aldehyde and pyrrole. Direct formation of the complex in this manner leads to an increase of the reaction yield by protecting the corrole ring toward oxidative decomposition. The procedure was successful and gave the expected product in the case of the copper and triphenylphosphinecobalt complexes, but an unexpected result was obtained in the case of the nickel derivative, where metal insertion led to a ring opening of the macrocycle at the 5 position, giving as a final product a linear tetrapyrrole nickel complex bearing two ferrocenyl groups. The purified 5,10,15-triferrocenylcorrole complexes have been fully characterized by a combination of spectroscopic methods, electrochemistry, spectroelectrochemistry, and density functional theory calculations. Copper derivatives of 10-monoferrocenyl- and 5,15-diferrocenylcorrole were prepared to investigate how the number and position of the ferrocenyl groups influenced the spectroscopic and electrochemical properties of the resulting complexes. A complete assignment of resonances in the (1)H and (13)C NMR spectra was performed for the cobalt and nickel complexes, and detailed electrochemical characterization was carried out to provide additional insight into the degree of communication between the meso-ferrocenyl groups on the conjugated macrocycle and the central metal ion of the ferrocenylcorrole derivatives.

show abstract

“…We have recently explored this topic through the synthesis and characterization of multiple corrole free bases bearing meso ‐ester groups . These particular substituents stabilize corrole free bases against oxidation and induce redshifts of their light absorption and emission bands.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Ruffled Phosphorus meso‐Ester Corroles

et al. 2016

Self Cite

View full text Add to dashboard Cite

The strong electron-withdrawing character of 5,15meso-ester groups was demonstrated through the study of four fluorescent hexacoordinate phosphorus(V) meso-substituted corroles, which were characterized by various techniques including single-crystal X-ray diffraction and first-principles calcu- [a] Compound 4-P: To a solution of 10-octadecyl-5,15-bis(ethoxycarbonyl)corrole (13 mg, 0.02 mmol) in dry pyridine (5 mL) was added POCl 3 (0.19 mL, 2 mmol), and the reaction mixture was heated to reflux for 30 min under argon. The solution color changed immediately from deep green to purple-violet with a greenish tint. The progress of the reaction was monitored by TLC analysis, and its completion was determined by absorption spectroscopy. After the completion of the reaction, the solvent was evaporated under reduced pressure. The crude solid was purified by silica gel chromatography (CH 2 Cl 2 /CH 3 OH 50:1), and the desired compound was collected from a greenish pink-violet band. The solvent was evaporated to afford a deep purple-violet solid (66 %, 10 mg, 0.013 mmol). R f = 0.75 (silica, CH 2 ] + 725.3826; found 725.3826.Compound 5-P: To a solution of 3-P (15 mg, 0.02 mmol) in dry tetrahydrofuran (THF, 10 mL) was added NaBH 4 (7.6 mg, 0.2 mmol), and the reaction mixture was heated to reflux for 1 h under argon. The progress of the reaction was monitored by TLC analysis, and its completion was determined by absorption spectroscopy. After the completion of the reaction, the reaction was quenched with a H 2 O/ MeOH mixture. The mixture was extracted with CHCl 3 . The organic layer was washed with brine and dried with anhydrous Na 2 SO 4 , and the solvents were evaporated to dryness. The crude solid was purified by silica gel chromatography (CH 2 Cl 2 /EtOAc 20:1). Compound 5-P was crystallized from CH 2 Cl 2 /n-heptane to afford a purple solid (30 %, 4 mg, 6 μmol). R f = 0.38 (silica gel, CH 2 Cl 2 ).

show abstract

meso‐Ester Corroles

Cited by 26 publications

References 124 publications

One‐Pot Synthesis of Contracted and Expanded Porphyrins with meso‐CF₃ Groups

One‐Pot Synthesis of Contracted and Expanded Porphyrins with meso‐CF₃ Groups

5,10,15-Triferrocenylcorrole Complexes

Synthesis and Characterization of Ruffled Phosphorus meso‐Ester Corroles

Contact Info

Product

Resources

About

meso‐Ester Corroles

Cited by 26 publications

References 124 publications

One‐Pot Synthesis of Contracted and Expanded Porphyrins with meso‐CF3 Groups

One‐Pot Synthesis of Contracted and Expanded Porphyrins with meso‐CF3 Groups

5,10,15-Triferrocenylcorrole Complexes

Synthesis and Characterization of Ruffled Phosphorus meso‐Ester Corroles

Contact Info

Product

Resources

About

One‐Pot Synthesis of Contracted and Expanded Porphyrins with meso‐CF₃ Groups

One‐Pot Synthesis of Contracted and Expanded Porphyrins with meso‐CF₃ Groups