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halogenated corrole

Christopher M Lemon, Seung Jun Hwang, Andrew G Maher, David C Powers, Daniel G Nocera
Main-group p-block metals are ideally suited for mediating two-electron reactions because they cycle between M n and M n+2 redox states, as the one-electron state is thermodynamically unstable. Here, we report the synthesis and structure of an SbIII corrole and its SbV X2 (X = Cl, Br) congeners. SbIII sits above the corrole ring, whereas SbV resides in the corrole centroid. Electrochemistry suggests interconversion between the SbIII and SbV X2 species. TD-DFT calculations indicate a HOMO → LUMO+2 parentage for excited states in the Soret spectral region that have significant antibonding character with respect to the Sb-X fragment...
May 7, 2018: Inorganic Chemistry
Joana F B Barata, M Graça P M S Neves, M Amparo F Faustino, Augusto C Tomé, José A S Cavaleiro
This review covers the functionalization reactions of meso-arylcorroles, both at the inner core, as well as the peripheral positions of the macrocycle. Experimental details for the synthesis of all known metallocorrole types and for the N-alkylation reactions are presented. Key peripheral functionalization reactions such as halogenation, formylation, carboxylation, nitration, sulfonation, and others are discussed in detail, particularly the nucleophilic aromatic substitution and the participation of corroles in cycloaddition reactions as 2π or 4π components (covering Diels-Alder and 1,3-dipolar cycloadditions)...
February 22, 2017: Chemical Reviews
Atif Mahammed, Biswajit Mondal, Atanu Rana, Abhishek Dey, Zeev Gross
A surprising effect of halide substituents on reduction potentials and catalytic activity of halogenated cobalt corroles has been deduced by experimental and computational methods; the proton-activating cobalt(I) and the cobalt(II) corrole that is formed in the step during which hydrogen is formed are characterized by NMR spectroscopy.
March 14, 2014: Chemical Communications: Chem Comm
Wenli Shao, Hui Wang, Shuang He, Lei Shi, Kaimei Peng, Yongfeng Lin, Lei Zhang, Liangnian Ji, Haiyang Liu
The luminescence, excited-state absorption, and singlet oxygen generation measurements were performed on three kinds of halogenated corroles: monohydroxyl halogenated corroles (Corrole-F, Corrole-Cl, Corrole-I), peripherally fluorine-substituted corroles (F0, F5, F10, F15), and gallium complexes (F10-Ga, F15-Ga). The fluorescence intensities progressively decrease whereas the triplet quantum yields, oxygen quenching rates, and singlet oxygen quantum yields increase with the increasing of the monohydroxyl halogen atomic weight...
December 13, 2012: Journal of Physical Chemistry. B
Alex Schechter, Maria Stanevsky, Atif Mahammed, Zeev Gross
The carbon-supported cobalt(III) complex of β-pyrrole-brominated 5,10,15-tris(pentafluorophenyl)corrole [Co(tpfc)Br(8)/C] is introduced as a nonplatinum alternative for electrocatalytic oxygen reduction in aqueous solutions. Through systematic work, the basic kinetic parameters of this reaction were studied, using rotating ring disk electrode electrochemical methods in the pH range of 0-11. Pronounced catalytic activity was detected in acid solutions along with shifts of the Co(II)/Co(III) and O(2) redox couples to more positive values (onset of 0...
January 2, 2012: Inorganic Chemistry
Luca Tortora, Sara Nardis, Frank R Fronczek, Kevin M Smith, Roberto Paolesse
Bromination of 3-nitro-5,10,15-triarylcorrole selectively provides two regioisomers, depending on the reaction pathway. An isocorrole species is the key intermediate to drive the reaction towards the 2-Br-17-nitro regioisomer.
April 14, 2011: Chemical Communications: Chem Comm
Romain Ruppert, Christophe Jeandon, Henry J Callot
Ring contraction of nickel meso-tetraarylporphyrins produced nonaromatic divalent corroles bearing a benzoyloxy function. We investigated their reactivity under electrophilic conditions: formylation, halogenation, nitration. We also found that the benzoate function could be eliminated to afford deoxocorroles, and we tested the formylation and nitration in this deoxo series. These corroles were generally very stable under the reaction conditions, and in both series, the directly bonded pyrroles were the most reactive...
January 18, 2008: Journal of Organic Chemistry
Liliya Simkhovich, Zeev Gross
The first full assignment of (1)H NMR chemical shifts for iron corroles and the first synthesis of a series of (halogeno)iron corroles reveal very large effects of the axial ligands on the corresponding spectra, which apparently reflect differences in the relative importance of metal-to-corrole and corrole-to-metal pi-donation. These findings pave the way for a thorough analysis of the electronic structures of such complexes.
October 4, 2004: Inorganic Chemistry
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