Visible light-driven photophysics and photochemistry of water-soluble metalloporphyrins

Horváth, Ottó; Valicsek, Zsolt; Fodor, Melinda A.; Major, Máté M.; Imran, Muhammad; Grampp, Günter; Wankmüller, Alexander

doi:10.1016/j.ccr.2015.12.011

Cited by 21 publications

(36 citation statements)

References 40 publications

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“…The most remarkable example is protoporphyrin IX and its iron complex that constitutes the heme prosthetic group and is crucial in oxygen transport. Metalloporphyrins are widely used in medicine, bio-sensing, catalysis and photocatalysis, optoelectronics and other fields [75][76][77].…”

Section: Metalloporphyrinsmentioning

confidence: 99%

Engineering of relevant photodynamic processes through structural modifications of metallotetrapyrrolic photosensitizers

Dąbrowski

Pucelik

Regiel-Futyra

et al. 2016

Coordination Chemistry Reviews

248

197

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Section: Metalloporphyrinsmentioning

confidence: 99%

Engineering of relevant photodynamic processes through structural modifications of metallotetrapyrrolic photosensitizers

Dąbrowski

Pucelik

Regiel-Futyra

et al. 2016

Coordination Chemistry Reviews

248

197

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“…Recently, Co and Ni complexes have also been photophysically investigated by Horváth et al as potential photocatalysts as well as for the functionalization of organic substrates by photocatalytic oxygenation in comparison to Mn(III) porphyrins [38][39][40]. The obtained results well demonstrated how the size of the metal center determines the structure and, thus, the photoinduced behavior of the porphyrin complexes, along with the substituents on the ligand.…”

mentioning

confidence: 78%

Photocatalytic Oxygenation by Water-Soluble Metalloporphyrins as a Pathway to Functionalized Polycycles

Šagud

Škorić

2018

International Journal of Photoenergy

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Photocatalytic processes are present in natural biochemical pathways as well as in the organic synthetic ones. This minireview will cover the field of photocatalysis that uses both the free-base and specially metallated porphyrins as catalysts. While free-base porphyrins are valuable sensitizers to output singlet oxygen, metalloporphyrins are even more adjustable as photocatalysts because of their coordination capacity, generating a wider range of oxidation reactions. They can be applied in autooxidation reactions, hydroxylations, or direct oxygen transfer producing epoxides. This review will mainly focus on how manganese and some iron porphyrins can be utilized for the functionalization of compounds that have a polycyclic skeleton in their structure. These kinds of compounds are notoriously taxing to obtain and difficult to further functionalize by conventional organic synthetic methods. We have focused on photocatalytic oxygenation reactions in mild conditions with the use of water-soluble porphyrins, as this has been proven to be a good tool for these transformations. In the photocatalytic reactions of some polycyclic heteroaromatic compounds, new polycyclic epoxides, enediones, ketones, alcohols, and/or hydroperoxides are yielded, depending on the catalyst applied. The application of anionic and cationic Mn(III) porphyrins under different reaction parameters results in different reaction pathways generating a vast number of photocatalytic products. Recently, Co and Ni complexes have been also photophysically investigated and confirmed as potential photocatalysts for the functionalization of organic substrates.

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“…Four pyrroles are connected through methylidine bridges, forming the porphin ring. Its planar structure with an extended conjugated π-electron system provides aromatic characteristics and a special coordination cavity for the binding of metal ions of suitable radius [1][2].…”

Section: Introductionmentioning

confidence: 99%

“…Overcrowded substitution on the periphery [3][4] or insufficiently short metal-nitrogen bonds due to the shrinkage of the coordination cavity can cause the ruffled or saddled deformation [2,[5][6][7]. If, however, the M-N bonds are significantly longer than half the length of the diagonal N-N distance in the free-base porphyrin, dome deformation can occur.…”

Section: Introductionmentioning

confidence: 99%

Formation, Photophysics, Photochemistry and Quantum Chemistry of the Out-of-Plane Metalloporphyrins

Valicsek¹,

Kiss²,

Fodor³

et al. 2017

Hungarian Journal of Industry and Chemistry

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Among the complexes of porphyrins, special attention has been paid to those possessing out-of-plane (OOP) structures, for the formation of which the size, as well as the coordinative character of the metal center are responsible. In these coordination compounds, the central atom cannot fit coplanarly into the cavity of the ligand, hence, it is located above the porphyrin plane, distorting it. Equilibria and kinetics of the complex formation, spectrophotometric, photophysical and primary photochemical properties of post-transition and lanthanide OOP metalloporphyrins were investigated, in addition electronic structural calculations were performed; hence, the general OOP characteristics were determined.Meanwhile, few doubtful questions have attempted to be answered concerning the categorization of metalloporphyrins, the borderline case complexes and hyperporphyrins.

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Visible light-driven photophysics and photochemistry of water-soluble metalloporphyrins

Cited by 21 publications

References 40 publications

Engineering of relevant photodynamic processes through structural modifications of metallotetrapyrrolic photosensitizers

Engineering of relevant photodynamic processes through structural modifications of metallotetrapyrrolic photosensitizers

Photocatalytic Oxygenation by Water-Soluble Metalloporphyrins as a Pathway to Functionalized Polycycles

Formation, Photophysics, Photochemistry and Quantum Chemistry of the Out-of-Plane Metalloporphyrins

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