262280-86-4

Upstream product

• 238402-21-6 5,10,15-tris(pentafluorophenyl)corrole 
• 6046-93-1 copper(II) acetate monohydrate 
• 925900-28-3 5,5'-((perfluorophenyl)methylene)bis(2-((perfluorophenyl)(1H-pyrrol-2-yl)methyl)-1H-pyrrole) 
• 142-71-2 copper diacetate 

Downstream Products

• 444987-91-1 Cu(C₁₉Br₈N₄(C₆F₅)3) 

Relevant academic research and scientific papers

Reactivity and Mechanism Studies of Hydrogen Evolution Catalyzed by Copper Corroles

Several copper corrole complexes were synthesized, and their catalytic activities for hydrogen (H2) evolution were examined. Our results showed that substituents at the meso positions of corrole macrocycles played significant roles in regulatin

Mechanochemical synthesis of freebase and metal corroles

Herein, we report on the mechanochemical reaction of pyrrole and substituted benzaldehyde precursors to produce freebase corroles and demonstrate the one-pot mechanochemical synthesis of 5,10,15-Tris(4-t-butylphenyl)corrole (H3t-buPhC), in which both, the

One-pot conversion of fluorophores to phosphorophores

Facile, one-pot conversion of free base 5,10,15-tris(pentafluorophenyl)corrole, (H3)tpfc, into the coinage metal complexes of 2,3,17,18-tetraiodo-5,10,15-tris(pentafluorophenyl)corrole, (I4-tpfc)M (M = Cu, Ag, Au), is reported. The iodination/metalation procedures provide much higher yields and larger selectivity than both conceivable stepwise syntheses. Photophysical analysis shows that the gold(III) complex (I4-tpfc)Au displays phosphorescence at room temperature and a substantial quantum yield for singlet oxygen formation.

Alkynyl corroles: Synthesis by Sonogashira coupling reaction and the physicochemical properties

Alkynyl corroles were synthesized from iodidphenyl corrole precursor by using Sonogashira coupling reaction with or without the presence of copper(I) iodide co-catalyst. The alkynyl group on corrole macrocycle has a significant effect on the photophysical and electrochemical properties of free-base and metal corrole derivatives.

Reductive demetallation of Cu-corroles - A new protective strategy towards functional free-base corroles

A novel procedure for the reductive demetallation of Cu-meso- triarylcorroles has been disclosed. The reversible sequence copper metallation/demetallation was proven to be an effective protection/deprotection strategy towards sophisticated functionalized

Electronic structures and reactivities of corrole-copper complexes

The spectroscopic and electrochemical examination of the mononuclear copper complexes of 5,10,15-tris(pentafluorophenyl)corrole and 5,10,15-tris(2,6- dichlorophenyl)corrole (1a and 2a, respectively) and of the corresponding dinuclear corrole dimers 1b and 2b reveal the existence of two almost degenerate electronic states. The lower state consists of copper(III) ions coordinated by closed-shell corrolato trianions and the higher state is composed of copper(II) ions chelated by open-shell corrolato dianions, The contributions from both states are evident in the molecular structure of monomeric and mononuclear 2a, which displays a distorted square-planar coordination geometry around the metal ion and short Cu-N bond lengths typical of copper(III), together with some non-equivalence of the Cα-Cmeso bond lengths that might reflect the open-shell character of the macrocycle. The latter state is most likely to be responsible for the dimerization process. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Electronic absorption, resonance Raman, and electrochemical studies of planar and saddled copper(III) meso-triarylcorroles. Highly substituent-sensitive Soret bands as a distinctive feature of high-valent transition metal corroles

We present here a first systematic study of substituent effects in metallocorroles, based on electronic absorption, resonance Raman (RR), and infrared (IR) spectroscopic studies and electrochemical measurements on 10 copper(III) meso-triarylcorroles, CuIII[β-Y8TArC], where the β-substituent Y = H or Br and the meso-aryl group Ar = C6F5 or p-X-C6H4 and X = CF3, H, CH3, and OCH3. The results afford a number of significant inisights. (1) The RR (and IR) results show that at least two and possibly more high-frequency bands in the 1400-1550 cm-1 region exhibit significant frequency downshifts on β-octabromination and, thus, qualify as structure-sensitive marker bands. DFT geometry optimizations indicate that the saddled conformation should be clearly preferred for the β-octabromo-meso-triarylcorrole derivatives studied and that β-octabromination results in expansion of a number of skeletal bond distances of the corrole macrocycle, consistent with observed frequency downshifts. (2) Electrochemical measurements on planar CuIII[TArC] derivatives have shown that the para substituents on the meso-aryl groups exert a strong influence on the half-wave potentials for oxidation (ρox = ΔE1/2ox/Δ(3σ) = 95 mV), suggesting that oxidation involves removal of an electron from the corrole "b1" HOMO, which has significant amplitudes at the meso postions and crudely resembles a porphyrin a2u HOMO in shape. In contrast, the Hammett ρox is much lower for the nonplanar CuIII[Br8TArC] derivatives and we suggest that this ultimately results from a b1-to-a2 HOMO reversal which in turn stems from a metal (dx2-y2)-corrole ("b1") orbital interaction that becomes symmetry-allowed under a saddle distortion of the corrole macrocycle. In contrast to what has been observed for metallotetraphenylporphyrins, β-octabromination dramatically raises the half-wave potential for one-electron oxidation of the triarylcorrole derivatives studied. This appears to be due to the fact that both the "a2" and "b1" HOMOs of a corrole (in C2v notation) have significantly higher amplitudes at the β positions, compared to a porphyrin a2u HOMO. Thus, although many metallocorroles are significantly more easily oxidizable than analogous metalloporphyrins, certain β-octahalogeno-meso-triarylcorrole derivatives can indeed be extremely electron deficient and oxidation resistant and may, therefore, find use as rugged catalysts or reagents under highly oxidizing conditions. (3) Finally, the Soret absorption maxima of high-valent metallotriarylcorroles exhibit a uniquely sensitive dependence on the substituents on the meso-aryl groups. Thus, on going from CuIII[T(p-CF3-P)C] (T(p-CF3-P)C = meso-tris((p-trifluoromethyl)phenyl)corrolato) to CuIII[T(p-OM-P)C] (T(p-OM-P)C = meso-tris(p-methoxyphenyl)corrolato), the Soret maximum red shifts by 26 nm, from 407 to 433 nm. Similarly, on going from CuIII[Br8T(p-CF3-P)C] (Br8T(p-CF3-P)C = β-octabromo- meso-tris((p-trifluoromethyl)phenyl)corrolato) to CuIII[Br8T(p-OM-P)C] (Br8T(p-CF3-P)C = β-octabromo-meso- tris(p-methoxyphenyl)corrolato), the Soret maximum red shifts by 34 nm, from 434 to 468 nm. Time-dependent DFT calculations suggest that this substituent dependence reflects significant ligand-to-metal charge-transfer character of certain transitions in the Soret region. The optical spectra of free-base and non-high-valent transition metal tetrapyrroles, in general, do not exhibit a similar substituent dependence.