Synthesis of a ‘face-to-face’ porphyrin-corrole. A potential precursor of a catalyst for the four-electron reduction of dioxygen

Jérôme, François; Gros, Claude P.; Tardieux, Catherine; Barbe, Jean‐Michel; Guilard, Roger

doi:10.1039/a805452e

Cited by 34 publications

(33 citation statements)

References 11 publications

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“…UV−visible data for the cofacial porphyrin−corrole complexes are given in the Experimental Section. As previously reported for the related (PCY)Co 2 complexes, ,, the PCB and PCX derivatives show electronic absorption spectra that are characterized by a blue-shifted Soret band and red-shifted visible bands as compared to the PCA and PCO analogues . These features are in good agreement with the cofacial geometry of the porphyrin and corrole rings and result from a larger interaction between the two metal macrocycles in the case of the PCB and PCX derivatives, which have a smaller interplanar distance between the two metal centers .…”

Section: Resultssupporting

confidence: 85%

Heterobimetallic Complexes of Cobalt(IV) Porphyrin−Corrole Dyads. Synthesis, Physicochemical Properties, and X-ray Structural Characterization

et al. 2005

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The synthesis of a novel family of heterobinuclear cofacial biphenylene (B), anthracene (A), 9,9-dimethylxanthene (X), or dibenzofuran (O) bridged porphyrin-corrole complexes, (PCY)MClCoCl, is reported, M being either an iron(III) or manganese(III) ion. Each complex was characterized by electrochemistry, mass spectrometry, UV-vis, IR, and electron spin resonance spectroscopy. Unlike previously examined biscobalt porphyrin-corrole dyads, the cobalt ion of the corrole moiety is present in a high-valence +4 oxidation state, as proven by electrochemistry, spectroelectrochemistry, and an X-ray diffraction study of (PCB)FeClCoCl, which shows the presence of a bound Cl- anion on the cobalt corrole. Structural data: (PCB)FeClCoCl x 0.5(C7H16) x 0.5(CH2Cl2) x 2H2O, triclinic, space group P1, a = 13.8463(3) A, b = 16.8164(5) A, c = 17.9072(6) A, alpha = 93.780(1) degrees, beta = 111.143(1) degrees, gamma = 97.463(2) degrees, Z = 2.

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Section: Resultssupporting

confidence: 85%

Heterobimetallic Complexes of Cobalt(IV) Porphyrin−Corrole Dyads. Synthesis, Physicochemical Properties, and X-ray Structural Characterization

et al. 2005

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“…All complexes of sufficient stability were characterized by UV-Vis and EPR spectroscopies. The cation of [FePh(OECorr)] was characterized structurally [94], and shows an identical p-p separation between two molecules as does the parent complex, 3.53 Å , a value considerably larger than that observed for the NO complex Based on prior work on cobalt bis-porphyrins, bis-chlorins, bis-corroles, porphyrin-chlorin and porphyrin-corrole (PC) heterodimers [102][103][104][105][106], a series of cobalt-iron or -manganese porphyrin-corrole dyads have been created and investigated by electrochemistry and spectroelectrochemistry. The cobalt is always in the corrole ring and the iron or manganese in the porphyrin ring.…”

Section: Electrochemical Reduction and Oxidation Of [Feno(oecorr)] [9mentioning

confidence: 99%

Iron corrolates: Unambiguous chloroiron(III) (corrolate)2− π-cation radicals

Walker

Licoccia

Paolesse

2006

Journal of Inorganic Biochemistry

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“…Multistep sequential syntheses have been described by Paolesse, Smith, Zheng, and co‐workers to afford directly unsymmetrical corrole–porphyrin dyads or those containing spacers with linkage through their meso ‐positions . Also, Guilard, Kadish, and co‐workers have described the electrochemistry, photophysics, and catalytic properties of several cofacial corrole–porphyrin hybrids containing different transition‐metal cations . Other synthetic pathways reported in the literature have involved the preparation of individual corrole and porphyrin moieties followed by their intermolecular linkage.…”

Section: Introductionmentioning

confidence: 99%

Engaging Copper(III) Corrole as an Electron Acceptor: Photoinduced Charge Separation in Zinc Porphyrin–Copper Corrole Donor–Acceptor Conjugates

Ngo

Zieba

Webre

et al. 2015

Chemistry A European J

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An electron-deficient copper(III) corrole was utilized for the construction of donor-acceptor conjugates with zinc(II) porphyrin (ZnP) as a singlet excited state electron donor, and the occurrence of photoinduced charge separation was demonstrated by using transient pump-probe spectroscopic techniques. In these conjugates, the number of copper corrole units was varied from 1 to 2 or 4 units while maintaining a single ZnP entity to observe the effect of corrole multiplicity in facilitating the charge-separation process. The conjugates and control compounds were electrochemically and spectroelectrochemically characterized. Computational studies revealed ground state geometries of the compounds and the electron-deficient nature of the copper(III) corrole. An energy level diagram was established to predict the photochemical events by using optical, emission, electrochemical, and computational data. The occurrence of charge separation from singlet excited zinc porphyrin and charge recombination to yield directly the ground state species were evident from the diagram. Femtosecond transient absorption spectroscopy studies provided spectral evidence of charge separation in the form of the zinc porphyrin radical cation and copper(II) corrole species as products. Rates of charge separation in the conjugates were found to be of the order of 10(10) s(-1) and increased with increasing multiplicity of copper(III) corrole entities. The present study demonstrates the importance of copper(III) corrole as an electron acceptor in building model photosynthetic systems.

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Synthesis of a ‘face-to-face’ porphyrin-corrole. A potential precursor of a catalyst for the four-electron reduction of dioxygen

Cited by 34 publications

References 11 publications

Heterobimetallic Complexes of Cobalt(IV) Porphyrin−Corrole Dyads. Synthesis, Physicochemical Properties, and X-ray Structural Characterization

Heterobimetallic Complexes of Cobalt(IV) Porphyrin−Corrole Dyads. Synthesis, Physicochemical Properties, and X-ray Structural Characterization

Iron corrolates: Unambiguous chloroiron(III) (corrolate)2− π-cation radicals

Engaging Copper(III) Corrole as an Electron Acceptor: Photoinduced Charge Separation in Zinc Porphyrin–Copper Corrole Donor–Acceptor Conjugates

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