Crystal and molecular structure of 21-thia-5,20-diphenyl-10,15-bis(p-nitrophenyl)-porphyrin and 21,23-dithiatetraphenylporphyrin. The influence of sulfur on the .pi.-delocalization pattern

Latos‐Grażyński, Lechosław; Lisowski, Jerzy; Szterenberg, Ludmiła; Olmstead, Marilyn M.; Balch, Alan L.

doi:10.1021/jo00012a044

Cited by 72 publications

(57 citation statements)

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“…In conclusion, dithiaethyneporphyrin-a new aromatic contracted porphyrinoid-has been synthesized and characterized and displays the unique features of an [18]dithiatriphyrin(4.1.1) frame.…”

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confidence: 99%

“…The aza-deficent porphyrin 5,10,15,20-tetraaryl-21-vacataporphyrin (butadieneporphyrin, [18]triphyrin(6.1.1); 1) is an annulene-porphyrin hybrid. [1] In principle, vacataporphyrin 1 (paradoxically expanded porphyrin) [2][3][4] can be considered as a seminal molecule for the subclass of triphyrins, which are distinguished by the fact that they contain only three pyrrole or pyrrole-like rings, linked by two sp 2 -hybridized meso carbon atoms to form the tripyrrolic brace.…”

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confidence: 99%

“…[5] Alternatively, the replacement of the six inner protons of [18]annulene by three oxygen, sulfur, or NH (NR) groups, or some combination of the three, as explored originally by Badger et al, leads to heteroatom-bridged annulenes 2; that is, [18]triphyrin(2.2.2) or [18]heterotriphyrin(2.2.2). [6][7][8] Herein, we report the synthesis and characterization of 3,8,13,18-tetraphenyl-19,21-dithiaethyneporphyrin (H(S 2 -ETPP); 3).…”

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confidence: 99%

“…[6][7][8] Herein, we report the synthesis and characterization of 3,8,13,18-tetraphenyl-19,21-dithiaethyneporphyrin (H(S 2 -ETPP); 3). This porphyrin derivative is a novel type of contracted heteroporphyrin related to putative [18]triphyrin-(4.1.1) with an acetylene moiety embedded in the macrocyclic framework. It introduces a unique structural pattern for contracted porphyrins, [2,4] created by fusing the structural motifs of 21,23-dithiaporphyrin and acetylene.…”

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confidence: 99%

“…[17] The S···S distance is short (3) ), and only a small number of compounds that contain such close sulfur-sulfur contacts have been reported. [13,[18][19][20] The C sp 2-C sp -C sp -C sp 2 butyne moiety reveals a slight distortion from linearity, showing a bowlike deformation directed outward of the macrocycle (C18-C1-C2: 174.0(9)8; C1-C2-C3: 176.6(9)8).…”

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confidence: 99%

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Dithiaethyneporphyrin: An Atypical [18]Triphyrin(4.1.1) Frame for Contracted Porphyrins

2005

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“…In conclusion, dithiaethyneporphyrin-a new aromatic contracted porphyrinoid-has been synthesized and characterized and displays the unique features of an [18]dithiatriphyrin(4.1.1) frame.…”

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Dithiaethyneporphyrin: An Atypical [18]Triphyrin(4.1.1) Frame for Contracted Porphyrins

2005

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Spectroscopic and Electrochemical Studies on Oxaporphyrins and Oxathiaporphyrins

Sridevi

Narayanan

Srinivasan

et al. 1998

J. Porphyrins Phthalocyanines

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The synthesis and characterization of oxaporphyrins ( OTPP and O 2 TPP ) containing one and two furan rings in place of pyrrole and a mixed oxathiaporphyrin ( OSTPP ) is reported. Spectroscopic and electrochemical studies reveal that oxaporphyrins exhibit optical and emission characteristics closer to the parent H 2 TPP , while their electrochemical behaviour parallels that reported for mono and dithiaporphyrins. However the characteristics of the mixed oxathia derivative resemble that of monothiaporphyrin. Protonation studies reveal weaker resonance interaction between the β-hydrogens and meso-phenyl substituents in sharp contrast to thiaporphyrins. The reduction potentials for OSTPP and O 2 TPP indicate stabilization and destabilization of their LUMOs relative to the parent H 2 TPP in the ground and excited states, respectively.

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Iron Porphyrin Chemistry

Walker¹,

Simonis²

2005

Encyclopedia of Inorganic Chemistry

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This article reviews most aspects of the chemistry of iron porphyrins, from Fe(0) to Fe(V), including occurrence and roles of natural iron porphyrins (hemes) and their synthetic analogs, structures and electron configurations of iron porphyrins of all oxidation and spin states, π electron configuration of the porphyrin ring, synthesis of metal‐free porphyrins and other related macrocycles, insertion of iron into free‐base porphyrins and related macrocycles, the properties, reactions, uses and biological relevance of iron(0), ‐(I), ‐(II) porphyrins (the latter with S = 0, 1, and 2 spin state possibilities), of iron(II) porphyrin π‐cation radicals, of iron(III) porphyrins (with S = 1/2, 3/2, and 5/2 spin state possibilities), of iron(III) porphyrin and corrole π‐cation radicals, of iron(IV) porphyrins (including five‐ and six‐coordinate ferryl (FeO) 2+ , iron(IV) phenyl, carbene and hydrazine complexes, and the bis‐methoxide complex) and a comparison of iron(IV) porphyrins to iron(III) porphyrin π‐cation radicals, of iron(IV) porphyrin π‐cation radicals, and of the possible existence of iron(V) porphyrins. Included in the Fe(II) part are sections on addition of ligands to four‐coordinate iron(II) porphyrins, including equilibrium binding constants, photodissociation of ligands from PFeL 2 complexes, binding of small molecules (O 2 , CO, NO, HNO) to 5‐coordinate iron(II) porphyrins and design of porphyrin ligands that will mimic the active sites of heme proteins such as myoglobin and hemoglobin, the cytochromes P450 and nitric oxide synthases, and the nitrophorins and guanylyl cyclases. Included in the iron(III) part are sections on both 5‐ and 6‐coordinate high‐spin complexes and their similarities and differences, bridged or through‐space magnetically coupled complexes of high‐spin iron(III) porphyrins with other metal complexes as possible models for cytochrome oxidase and the assimilatory sulfite reductases, coupled oxidation of hemes by hydrogen peroxide or its equivalent, and the relationship of this reactivity to the reactions of heme oxygenase, iron(III) porphyrins as reduction catalysts, and photochemistry of iron(III) porphyrins, possible electron configurations of low‐spin iron(III) porphyrins, the phenomenon and possible electronic consequences of ruffling of the porphinato core in iron(III) porphyrins, the preferred orientation of planar axial ligands bound to low‐spin iron(III) porphyrins, NO complexes of iron(III) porphyrins, reduction potentials, equilibrium constants and rates of axial‐ligand addition and exchange, kinetics of axial‐ligand rotation and porphyrin ring inversion, kinetics of reduction and autoreduction of iron(III) porphyrins, electron self‐exchange between low‐spin iron(III) and iron(II) porphyrins, synthetic ferriheme proteins, and synthesis of five‐coordinate low‐spin iron(III) porphyrins having σ‐alkyl or σ‐aryl groups as axial ligands. The iron(IV) and iron(IV) cation radical sections discuss the high‐valent states of cytochromes P450 and related enzymes.

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Crystal and molecular structure of 21-thia-5,20-diphenyl-10,15-bis(p-nitrophenyl)-porphyrin and 21,23-dithiatetraphenylporphyrin. The influence of sulfur on the .pi.-delocalization pattern

Cited by 72 publications

References 2 publications

Dithiaethyneporphyrin: An Atypical [18]Triphyrin(4.1.1) Frame for Contracted Porphyrins

Dithiaethyneporphyrin: An Atypical [18]Triphyrin(4.1.1) Frame for Contracted Porphyrins

Spectroscopic and Electrochemical Studies on Oxaporphyrins and Oxathiaporphyrins

Iron Porphyrin Chemistry

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