Structure and catalytic activity of a manganese(<scp>iii</scp>) tetraphenylporpholactone

Çetin, Anıl; Ziegler, Christopher J.

doi:10.1039/b417321j

Cited by 26 publications

(29 citation statements)

References 14 publications

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“…We previously also demonstrated the applicability of this method to the synthesis of dithiaporphyrin- and porphyrin N -oxide-based porpholactones. 17,18 As also shown previously, 6,10,11,12 additional metalloporpholactones are available through metal insertions into the free bases using standard methods (using conventional and microwave heating).…”

Section: Resultssupporting

confidence: 58%

“…A comparison of the Ni(II), Cu(II), Fe(III), and Mn(III) complexes of porphyrins 39 and porpholactones 6,7,10 show also their overall similarity with respect to the respective overall macrocycle conformation. The C=O bond length in the zinc porpholactone 5aZn is 1.26 Å and the C-O bond length is 1.40 Å.…”

Section: Resultsmentioning

confidence: 92%

“…The crystal structures of [porpholactonato]Mn(III)Cl, 10 Fe(III)Cl, 6 Cu(II), 7 and Ni(II) 7 complexes are known. Thus, the connectivity of the porpholactones is not in question.…”

Section: Resultsmentioning

confidence: 99%

“…14,16-19,20 This reaction was adopted by other groups, providing a range of dihydroxychlorins. 10,11,21-23 We further demonstrated the versatility of the chlorin diols as starting material for the preparation of porphyrinoids containing non-pyrrolic building blocks using our versatile ‘breaking and mending’ strategy. 9,14-18,24,25 The synthesis of porpholactones via the MnO 4 − -mediated oxidation of the known meso -tetraaryl-2,3-dihydroxychlorins also follows this strategy.…”

Section: Introductionmentioning

confidence: 90%

“…6 The catalytic activity of the Fe(III)Cl and Mn(III)Cl complexes of meso -tetrakis(phenyl)porpholactone with respect to olefin epoxidation and sulfide oxidation reactions were tested. 10,11 [ meso -Tetrakis(pentafluorophenyl)porpholactonato]Pt(II) is a promising component in pressure sensitive paints, 12 allowing the imaging of air flow around objects. 13 This complex can also be utilized as a high pH sensor in the range of pH 11.5–13.…”

Section: Introductionmentioning

confidence: 99%

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meso-Arylporpholactones and their Reduction Products

et al. 2012

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The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO 4 − mediated oxidations of the corresponding meso-tetraaryl-2,3dihydroxychlorins ( 7) is detailed. Since chlorin 7 is prepared from the parent porphyrin 1, this amounts to a 2-step replacement of a pyrrole moiety in 1 by an oxazolone moiety. The stepwise reduction of the porpholactone 5 results in the formation of chlorin analogues, meso-tetraaryl-3-hydroxy-2oxachlorin ( 11) and meso-tetraaryl-2-oxachlorins (12). The reactivity of 11 with respect to nucleophilic substitution by O-, N-, and S-nucleophiles is described. The profound photophysical consequences of the formal replacement of a pyrrole with an oxazolone (porphyrin-like chromophore) or (substituted) oxazole moiety (chlorin-like chromophore with, for the parent oxazolochlorin 12, red-shifted Q x band with enhanced oscillator strengths) are detailed and rationalized on the basis of SAC−CI and MNDO-PSDCI molecular orbital theory calculations. The single crystal X-ray structures of the porpholactones point at a minor steric interaction between the carbonyl oxygen and the flanking phenyl group. The essentially planar structures of all chromophores in all oxidation states prove that the observed optical properties originate from the intrinsic electronic properties of the chromophores and are not subject to conformational modulation.

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Section: Resultssupporting

confidence: 58%

Section: Resultsmentioning

confidence: 92%

“…The crystal structures of [porpholactonato]Mn(III)Cl, 10 Fe(III)Cl, 6 Cu(II), 7 and Ni(II) 7 complexes are known. Thus, the connectivity of the porpholactones is not in question.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

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meso-Arylporpholactones and their Reduction Products

et al. 2012

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Oxidation and Reduction of Porphyrins

Brückner

Hewage

2022

Fundamentals of Porphyrin Chemistry

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Ruthenium‐Catalyzed Oxidation of the Porphyrin β,β′‐Pyrrolic Ring: A General and Efficient Approach to Porpholactones

et al. 2012

Adv Synth Catal

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We describe an efficient ruthenium‐catalyzed oxidation of the β,β′‐pyrrolic ring on the porphyrin periphery. Through the conversion of a β,β′‐double bond to a lactone moiety, the direct preparation of porpholactones from porphyrins is achieved, which previously suffered from needing toxic reagents, multiple synthetic steps and low yields. The generality of this method has been investigated with various porphyrins with different electronic and steric effects, even some metalloporphyrins, and so represents a general and efficient approach for the synthesis of the intriguing porpholactone derivatives.

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Structure and catalytic activity of a manganese(iii) tetraphenylporpholactone

Cited by 26 publications

References 14 publications

meso-Arylporpholactones and their Reduction Products

meso-Arylporpholactones and their Reduction Products

Oxidation and Reduction of Porphyrins

Ruthenium‐Catalyzed Oxidation of the Porphyrin β,β′‐Pyrrolic Ring: A General and Efficient Approach to Porpholactones

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