Corrole chemistry has witnessed an impressive boost in studies in the last 20 years, thanks to the possibility of preparing corrole derivatives by simple synthetic procedures. The investigation of a large number of corroles has highlighted some peculiar characteristics of these macrocycles, having features different from those of the parent porphyrins. With this progress in the elucidation of corrole properties, attention has been focused on the potential for the exploitation of corrole derivatives in different important application fields. In some areas, the potential of corroles has been studied in certain detail, for example, the use of corrole metal complexes as electrocatalysts for energy conversion. In some other areas, the field is still in its infancy, such as in the exploitation of corroles in solar cells. Herein, we report an overview of the different applications of corroles, focusing on the studies reported in the last five years. 

Corroles at work: a small macrocycle for great applications

Two fluorinated meso-C6F5-corroles (5,15-bis(pentafluorophenyl)-10-(phenyl)corrole and 5,15-bis(pentafluorophenyl)-10-(1-pyrenyl)corrole) were biologically evaluated in terms of binding affinity to...

Fluorescent pyrene moiety in fluorinated C6F5-corroles increases the interaction with HSA and CT-DNA

The extraordinary potential of hydrogen as a clean and sustainable fuel has sparked the interest of the scientific community to find environmentally friendly methods for its production. Biological catalysts are the most attractive solution, as they usually operate under mild conditions and do not produce carbon-containing byproducts. Hydrogenases promote reversible proton reduction to hydrogen in a variety of anoxic bacteria and algae, displaying unparallel catalytic performances. Attempts to use these sophisticated enzymes in scalable hydrogen production have been hampered by limitations associated with their production and stability. Inspired by nature, significant efforts have been made in the development of artificial systems able to promote the hydrogen evolution reaction, via either electrochemical or light-driven catalysis. Starting from small-molecule coordination compounds, peptide- and protein-based architectures have been constructed around the catalytic center with the aim of reproducing hydrogenase function into robust, efficient, and cost-effective catalysts. In this review, we first provide an overview of the structural and functional properties of hydrogenases, along with their integration in devices for hydrogen and energy production. Then, we describe the most recent advances in the development of homogeneous hydrogen evolution catalysts envisioned to mimic hydrogenases.

/pdf/enzymatic-and-bioinspired-systems-for-hydrogen-production-2i4klj09.pdf

Enzymatic and Bioinspired Systems for Hydrogen Production

Electrocatalytic hydrogen evolution of manganese corrole

A new Cu porphyrin bearing meso -( o -carborane) substituents is designed and synthesized and displays much higher activity than o -carborane-free analogues for the electrocatalytic hydrogen evolution reaction in both organic and aqueous solutions. 

Electrocatalytic hydrogen evolution with a copper porphyrin bearing meso-(o-carborane) substituents.

The photophysical properties of a series of pyridyl corroles were reported. Their excited-state dynamics were investigated by femtosecond transient absorption, which revealed a very fast intersystem crossing in the tin complex (3.9 × 109 s−1) with a high triplet yield of 0.91. An accelerated vibrational cooling of free-base corrole in DMF was observed due to deprotonation. The ability of these corroles to generate singlet oxygen was also quantitatively measured, which demonstrated the tin complex as a promising photosensitizer. The photo-induced reactive oxygen species (ROS) were detected by EPR. Additionally, the DNA binding affinity of these corroles was evaluated to inspect their potential biological use.

Photophysical properties, singlet oxygen generation and DNA binding affinity of Tris(4-pyridyl)corrole and its phosphorous, gallium and tin complexes

Catalytic oxidation using manganese corrole is a hot topic of contemporary porphyrin chemistry, in which PhIO, TBHP, PhI(OAc)2, KHSO5 and m-CPBA are usually used as oxidants. This article reports the first selective oxidation of styrene to benzaldehyde using a manganese(III) corrole catalyst and sodium nitrite (NaNO2) as oxidant and cocatalyst at room temperature. The yield was 158.1% in air and 96.5% under a nitrogen atmosphere, showing oxygen might be involved in the reaction and that NaNO2 is an oxygen source and cocatalyst in the system. The peripheral electron-withdrawing substituents of the manganese corrole were favorable to the catalytic reaction. Radical inhibition and H218O experiments proved that the catalytic reaction was a free radical and hydrolysis-involved reaction.

Manganese corrole catalyzed selective oxidation of styrene to benzaldehyde: sodium nitrite functions as an oxidant and cocatalyst.

Corrole can offer the advantages of strong optical nonlinearity and fast optical response, because of its highly conjugated π-electron distribution and the reduced symmetry as compared to porphyrin, and it has been studied as a new kind of nonlinear optical materials recently. Gallium corroles are highly fluorescent, of which the two-photon excited emission may facilitate the treatment of deep-seated tumors. This is the first report of two-photon absorption (TPA) spectrum of corrole gallium complex, and single- and two-photon absorption properties of three gallium corroles (F10Ga, F15Ga, and F15GaS) have been studied to explore the effects of solvent and peripheral substituent on the TPA properties of gallium corrole. Larger TPA intensities of F10Ga and F15Ga are obtained in polar solvent DMF compared to nonpolar solvent toluene. The introduction of two sulfonated groups results in a decrease in TPA intensity, which may be associated with an increase in symmetry. Nonplanar distortion produced for the absence of one penta-fluorophenyl group however leads to a TPA enhancement. These results may be instructive for the development of corroles to be used in the areas of cancer diagnosis and therapy. 

Single- and two-photon absorption properties of gallium corroles

Light-Induced Electron Transfer in Manganese(V)–Oxo Corroles

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