The metal complexes of N-confused porphyrin as heme model compounds

Harvey, J.D.; Ziegler, Christopher J.

doi:10.1016/j.jinorgbio.2006.01.016

Cited by 59 publications

(40 citation statements)

References 49 publications

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“…Removal of excess pyrrole, followed by column chromatography on silica gel (CH 2 Cl 2 /hexane 6:4 (v/v)), afforded isomer I as an off-white foamlike solid (72 %, 0.58 g, 0.72 mmol). 1 H NMR (CDCl 3 , 300 MHz): d = 5.70 (s, 1 H), 5.72 (s, 1 H), 5.82-5.86 (m, 3 H), 5.92-5.95 (m, 2 H), 6.12-6.15 (m, 2 H), 6.45 (s, 1 H), 6.62 (s, 1 H), 6.71 (d, J = 1.2 Hz, 1 H), 6.78 (d,J = 2.7 Hz,1 H),4 H); 13 C NMR (CDCl 3 , 75 MHz) : d = 32.6, 32.8, 33.5, 106.6, m 107.1, m 107.7, d 108.4, d 108.7, 109.0, d 115.7, d 116.2, f 116.9, d 118.0, f 118.2, m 119.2, 121.3, m 121.7, m 127.4, m 128.6, m 131.6, m 37 H 27 F 15 N 4 : C 55.37, H 2.14, N 6.98; found: C 55.70, H 2.17, N 6.93.…”

Section: Methodsmentioning

confidence: 99%

“…Removal of the solvent, followed by column chromatography on silica gel (CH 2 Cl 2 /hexane 6:4 A C H T U N G T R E N N U N G (v/v)), afforded 3 as a pale yellow, foamlike solid (79 %, 1.42 g, 1.56 mmol). 1 H NMR (CDCl 3 , 300 MHz): d = 1.07 (d,J = 7.5 Hz,9 H),1.08 (d,J = 7.5 Hz,9 H) : d = 11.6, 17.7, 32.3, 32.7, 106.2, d 110.2, 110.9, 114.0, f 115.5, d Figure 4. X-ray structure of the doubly N-confused biladiene copper(II) complex (28).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis and Reactivity of 5,10,15‐Triaryl Doubly N‐Confused Bilanes

Toganoh¹,

Gokulnath²,

Kawabe³

et al. 2012

Chemistry A European J

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A series of 5,10,15-tris(pentafluorophenyl) doubly N-confused bilanes were synthesized in a stepwise manner with the aid of sterically demanding N-protecting groups, in which the difference in reactivity between regular pyrrole and N-confused pyrrole plays a crucial role in the synthetic strategy. Some doubly N-confused bilanes were converted into porphyrinoids or a unique 2:2 copper(II) complex with a helical structure. In addition, the conformations and electronic states of the doubly N-confused bilanes were investigated theoretically, giving fruitful information about the effect of confusion on the bilane skeleton.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Synthesis and Reactivity of 5,10,15‐Triaryl Doubly N‐Confused Bilanes

Toganoh¹,

Gokulnath²,

Kawabe³

et al. 2012

Chemistry A European J

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“…N-Confused porphyrins have attracted a great deal interest [1][2][3][4][5][6][7][8][9] since the first synthesis of these compounds was independently reported by the groups of Furuta [10] and Latos-Grazynski [11] in 1994. N-Confused porphyrins are structurally similar to "normal" porphyrins, but have an inverted pyrrole with a carbon inside the cavity and a nitrogen on the periphery of the p-system as shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Effect of Solvent and Protonation/Deprotonation on Electrochemistry, Spectroelectrochemistry and Electron‐Transfer Mechanisms of N‐Confused Tetraarylporphyrins in Nonaqueous Media

Xue

et al. 2014

Chemistry A European J

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A series of N-confused free-base meso-substituted tetraarylporphyrins was investigated by electrochemistry and spectroelectrochemistry in nonaqueous media containing 0.1 M tetra-n-butylammonium perchlorate (TBAP) and added acid or base. The investigated compounds are represented as (XPh)4 NcpH2 , in which "Ncp" is the N-confused porphyrin macrocycle and X is a OCH3 , CH3 , H, or Cl substituent on the para position of each meso-phenyl ring of the macrocycle. Two distinct types of UV/Vis spectra are initially observed depending upon solvent, one corresponding to an inner-2H form and the other to an inner-3H form of the porphyrin. Both forms have an inverted pyrrole with a carbon inside the cavity and a nitrogen on the periphery of the π-system. Each porphyrin undergoes multiple irreversible reductions and oxidations. The first one-electron addition and first one-electron abstraction are located on the porphyrin π-ring system to give π-anion and π-cation radicals with a potential separation of 1.52 to 1.65 V between the two processes, but both electrogenerated products are unstable and undergo a rapid chemical reaction to give new electroactive species, which were characterized in the present study. The effect of the solvent and protonation/deprotonation reactions on the UV/Vis spectra, redox potentials and reduction/oxidation mechanisms is discussed with comparisons made to data and mechanisms for the structurally related free-base corroles and porphyrins.

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“…[20] Porphyrinoids with inverted porphyrin platform H 2 IP (2-aza-21-carbaporphyrin derivatives) [21,22] attract a great interest through its unique molecular structure. [23][24][25][26][27][28][29][30][31] Water soluble N-confused porphyrin derivatives are very interesting objects for researchers due to their potential medical and biological application. [32][33][34][35][36] Previously it was established that porphyrinoids with inverted pyrrole ring possess an ability to form anion complexes [ 4 ] n [39] in acidic media.…”

Section: +mentioning

confidence: 99%