Synthesis of Corroles and Their Heteroanalogs

Orłowski, Rafał; Gryko, Dorota; Gryko, Daniel T.

doi:10.1021/acs.chemrev.6b00434

Cited by 233 publications

(148 citation statements)

References 202 publications

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“…The purification protocol also showed considerable difficulties, because it was necessary to remove even traces of the residual oxidant, and the following chromatographic purification of 9 should be very fast, to avoid its chemisorption onto the silica used for the chromatographic column. With a careful control of these steps we were able to obtain the target corrole in a 10 % yield, which is comparable with those of several triarylcorroles …”

Section: Resultsmentioning

confidence: 99%

“…In order to increase the yield of the aryl‐sulfonated corrole, based on the results obtained in our previous work for the mono phenyl‐substituted compound, we carried out the reaction on the corresponding phosphorus complex, since the P is able to reduce the corrole ring reactivity towards the electrophilic substitution. This has allowed us to obtain for the first time the P complex of 2 , albeit as minor product and only in acceptable yields for corrole functionalizations (9 %) …”

Section: Introductionmentioning

confidence: 99%

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5,10,15‐Tris(4‐sulfonatophenyl)corrole Synthesis

et al. 2019

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Two synthetic routes for the preparation of the water soluble 5,10,15‐tris(4‐sulfonatophenyl)corrole are reported. The first approach explores the chlorosulfonation reaction on the phosphorus complex of 5,10,15‐tris(4‐trimethylsilylphenyl)corrole. Following this route, the P complex of the target corrole has been obtained in low yields, while the major product was the tetrasubstituted complex, with the additional sulfonyl group regioselectively introduced at the 2‐position. To widen the scope of the reaction, the direct preparation of the 5,10,15‐tris(4‐sulfonatophenyl)corrole has been pointed out, affording both the target corrole and the intermediate chlorosulfonyl derivative in reasonable yields. The photophysical properties and the protonation equilibria of both corroles have been investigated, showing that 5,10,15‐tris(4‐sulfonatophenyl)corrole does not aggregate in acidic solutions, different from the analogous porphyrin.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

5,10,15‐Tris(4‐sulfonatophenyl)corrole Synthesis

et al. 2019

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“…Corroles are tetrapyrrolic macrocycles that are closely related to porphyrins, with one carbon less in the outer periphery and one NH proton more in their inner core , . Thus, unlike porphyrins, corroles have one direct pyrrole–pyrrole linkage that results in a smaller cavity than that of porphyrins , . However, because of the presence of three inner NH atoms, corroles have a greater ability to stabilize metals formally in higher oxidation states than porphyrins .…”

Section: Introductionmentioning

confidence: 99%

“…Thus, unlike porphyrins, corroles have one direct pyrrole–pyrrole linkage that results in a smaller cavity than that of porphyrins , . However, because of the presence of three inner NH atoms, corroles have a greater ability to stabilize metals formally in higher oxidation states than porphyrins . The corrole chemistry has gained tremendous momentum after the breakthrough discoveries of simple synthetic strategies for the preparation of corroles with readily available precursors , .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of ABC‐Type 22‐Oxacorroles Bearing Three Different Five‐Membered Heterocycles at the meso Positions

2019

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The acid‐catalyzed [3+2] condensation of appropriate tripyrrane and dipyrromethane yields first examples of two novel ABC type 22‐oxacorroles containing three different types of five‐membered heterocycles such as pyrrole, thiophene, and furan at three meso‐positions in 8–12 % yields. The two 22‐oxacorroles were characterized by HR‐MS, 1D & 2D NMR spectroscopy, absorption, fluorescence, electrochemical and DFT studies. The absorption maxima and quantum yields of the oxacorroles were found to be dependent on the relative positions of meso‐heteroaryl substituents and absorption bands appeared in the region of 410–660 with low quantum yields (0.08–0.14). The electrochemical and DFT studies reveal that the redox properties of 22‐oxacorroles were significantly altered by replacing six‐membered meso‐aryl groups with three different heterocycles. The meso‐heteroaryl substituents such as furyl, pyrrolyl and thienyl groups were aligned with respect to the plane of macrocycles with varying degrees of dihedral angles.

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“…Corroles are porphyrin analogues containing direct pyrrole–pyrrole linkages, three interior N–H protons and smaller cores compared with those of porphyrins. They can stabilize the higher oxidation states of metals . After the development of the Gryko corrole synthesis, which allows the large‐scale preparation of meso ‐substituted corroles, limited numbers of porphyrin–corrole conjugates were synthesized with different types of bridges at the meso positions of the macrocycles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic Properties, and DFT Calculations of Imine‐Bridged meso–meso‐ and β‐meso‐Linked Porphyrin–Corrole Dyads

2017

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The first imine‐bridged meso–meso‐ and β‐meso‐linked porphyrin–corrole dyads were prepared, and their photophysical properties were investigated by UV/Vis and fluorescence spectroscopy. To gain more insights into the geometric structures and the frontier molecular orbitals of the newly synthesized structures, DFT calculations at the B3LYP/6‐311G(d,p) level in the gas phase and with toluene as the solvent were performed. The theoretical results indicate that the imine‐bridged dyads possess well‐defined charge separation between the porphyrin and corrole moieties; therefore, intramolecular electron transfer from the corrole to the porphyrin ring is favoured.

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Synthesis of Corroles and Their Heteroanalogs

Cited by 233 publications

References 202 publications

5,10,15‐Tris(4‐sulfonatophenyl)corrole Synthesis

5,10,15‐Tris(4‐sulfonatophenyl)corrole Synthesis

Synthesis of ABC‐Type 22‐Oxacorroles Bearing Three Different Five‐Membered Heterocycles at the meso Positions

Synthesis, Spectroscopic Properties, and DFT Calculations of Imine‐Bridged meso–meso‐ and β‐meso‐Linked Porphyrin–Corrole Dyads

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