Photoredox and photocatalytic characteristics of various iron meso-tetraarylporphyrins

Bartocci, C.; Maldotti, Andrea; Varani, G.; Battioni, Pierrette; Carassiti, V.; Mansuy, Daniel

doi:10.1021/ic00006a018

Cited by 52 publications

(34 citation statements)

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“…The UV/Vis absorption spectrum after 10 min of visible-light irradiation was restored gradually to the original UV/Vis absorption spectrum of [Fe III (TPFPP)OH] in the dark with isosbestic points; however, the absorbance of the restored spectrum was not perfectly consistent with that of the original spectrum because a small amount of [Fe III (TPFPP)OH] decomposed under irradiation. Bartocci et al [17] reported that the reversible peak change is com- Figure 9 a and b. However, a substrate such as cyclohexene inhibits the decrease in the Soret band of [Fe II (TPFPP)] because epoxidation proceeds in preference to autolysis (Figure 9 c).…”

Section: Resultsmentioning

confidence: 98%

Photoactivation of Molecular Oxygen by an Iron(III) Porphyrin with a Magnesium Aluminum Layered Double Hydroxide for the Aerobic Epoxidation of Cyclohexene

et al. 2014

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The photocatalytic aerobic epoxidation of cyclohexene proceeded under visible‐light irradiation only if 5,10,15,20tetrakis(pentafluorophenyl)porphyrin iron(III) chloride ([FeIII(TPFPP)Cl]) was combined with Mg‐Al layered double hydroxide (Mg‐Al LDH) as a solid base in chloroform. The OH groups in the Mg‐Al LDH exchanged with the axial Cl ligands in [FeIII(TPFPP)Cl] to afford [FeIII(TPFPP)OH], which functioned photocatalytically in the presence of Mg‐Al LDH but was inactive in its absence. The band in the action spectrum agreed well with the Soret band in the UV/Vis absorption spectrum of [FeIII(TPFPP)OH]. The spectral changes indicated the reduction of [FeIII(TPFPP)OH] to [FeII(TPFPP)] under visible‐light irradiation, which in turn activates O2 that could be used for the epoxidation of cyclohexene.

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Section: Resultsmentioning

confidence: 98%

Photoactivation of Molecular Oxygen by an Iron(III) Porphyrin with a Magnesium Aluminum Layered Double Hydroxide for the Aerobic Epoxidation of Cyclohexene

et al. 2014

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“…[3] Moreover, they provide a steric protection of the porphyrin ring against its radical-induced oxidative degradation. [4] One intriguing and up-to-date aspect of the photocatalytic processes described above is their possibility to generate reactive intermediates such as Fe…”

Section: Introductionmentioning

confidence: 99%

“…The subsequent OϪO bond scission yields a presumed iron-oxo species that is able to hydroxylate a guanidinic nitrogen of -arginine. (4) The second step involves an oxidative cleavage of the Cϭ NOH bond of N-hydroxy--arginine to give the final products NO and -citrulline through the consumption of one mol of O 2 and only one electron coming from 0.5 mol of NADPH [second step in Equation (4) (P) in their starting conditions (step c).…”

Section: Introductionmentioning

confidence: 99%

“…We decided to use an acetone/ethanol (95:5) mixture as solvent knowing that, in these conditions, ethanol works as coordinating solvent and that the primary photochemical process is expected to be the reduction of Fe III to Fe II by the bound ethanolate, in line with the general mechanism shown in Equation (1). [2,4] Accordingly, the UV/Vis spectrum observed after irradiation (Curve A in Figure 5) presents the typical absorption at 567 nm of the ferrous porphyrin. The spectral changes (Curve B) that accompany the subsequent oxygenation of the sample at low temperature (Ϫ5 to Ϫ8°C) are consistent with the forma- Figure 5 shows that this oxygenation/deoxygenation cycle is not completely reversible, probably due to irreversible oxidation of the porphyrin ring.…”

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Oxidation of N‐(4‐Chlorophenyl)‐N′‐hydroxyguanidine to N‐(4‐Chlorophenyl)urea and Nitric Oxide by Photoexcited Iron Porphyrins

et al. 2004

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Photochemical excitation (λ > 350 nm) of chloro[meso‐tetrakis(2,6‐dichlorophenyl)porphyrin]iron(III) [FeIII(TDCPP)Cl] and chloro[meso‐tetra(α,α,α,α‐pivalamidophenyl)porphyrin]iron(III) [FeIII(TpivPP)Cl] induces the oxidation of coordinated N‐(4‐chlorophenyl)‐N′‐hydroxyguanidine (1) by molecular oxygen, to give iminoxyl radicals and the FeII(O2) [or FeIII(O2·)] adduct. This complex can be accumulated in significant amounts using [FeIII(TpivPP)Cl]. The primary photoproducts give rise to secondary reactions that lead to the formation of N‐(4‐chlorophenyl)urea (2) as the main end‐product of 1. The conversion of 1 into 2 is accompanied by the formation of NO, as revealed both by an ESR spin‐trapping technique and in the form of its stable end‐products NO2− and NO3−. The presence of 1‐methyl imidazole (1‐MeIm) coordinated in axial position has a significant positive effect on the photoinduced production of 2 and NO from the hydroxyguanidine 1. The observation that radical scavengers inhibit the photooxidation process strongly supports the possibility that the reaction pathway resembles a radical‐type autoxidation mechanism, where the very fast reaction of O2 with the ferrous porphyrin in the presence of the photogenerated iminoxyl radical should yield an iron‐peroxo intermediate as precursor of the urea 2 and NO. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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“…[9] play a fundamental role in controlling both the efficiency and the selectivity of the catalytic process. In this framework, we have recently reported that photoexcitation of…”

Section: Introductionmentioning

confidence: 99%

Photocatalyzed Oxidation of Cyclohexene and Cyclooctene with (nBu4N)4W10O32 and (nBu4N)4W10O32/FeIII[meso-Tetrakis(2,6-dichlorophenyl)porphyrin] in Homogeneous and Heterogeneous Systems

Molinari¹,

Амаделли²,

Carassiti³

et al. 2000

Eur. J. Inorg. Chem.

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Photoredox and photocatalytic characteristics of various iron meso-tetraarylporphyrins

Cited by 52 publications

References 0 publications

Photoactivation of Molecular Oxygen by an Iron(III) Porphyrin with a Magnesium Aluminum Layered Double Hydroxide for the Aerobic Epoxidation of Cyclohexene

Photoactivation of Molecular Oxygen by an Iron(III) Porphyrin with a Magnesium Aluminum Layered Double Hydroxide for the Aerobic Epoxidation of Cyclohexene

Oxidation of N‐(4‐Chlorophenyl)‐N′‐hydroxyguanidine to N‐(4‐Chlorophenyl)urea and Nitric Oxide by Photoexcited Iron Porphyrins

Photocatalyzed Oxidation of Cyclohexene and Cyclooctene with (nBu4N)4W10O32 and (nBu4N)4W10O32/FeIII[meso-Tetrakis(2,6-dichlorophenyl)porphyrin] in Homogeneous and Heterogeneous Systems

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