1983
DOI: 10.1021/ja00348a018
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Synthesis and characterization of the "pocket" porphyrins

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1985
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Cited by 109 publications
(74 citation statements)
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“…However, the 1 H-NMR spectrum of these species is not as well-defined as with CObound or O 2 -bound species (33,34) suggesting that multiple species with different spin states may be present. Upon drying the sample by azeotropic distillation with toluene the following observations were made: (i) paramagnetic signals develop first at 15 ppm then at 50-60 ppm corresponding to the signals of ␤-pyrrole protons (35)(36)(37)(38) and (ii) the 4 band of a high spin species develops (1,342 cm Ϫ1 ) to give a 3:7 ratio 4 band(HS)/4 band(LS). However, washing a dry sample with water resulted in the disappearance of both the 1 H-NMR paramagnetic signals and the resonance Raman 4 high spin marker band.…”
Section: Resultsmentioning
confidence: 99%
“…However, the 1 H-NMR spectrum of these species is not as well-defined as with CObound or O 2 -bound species (33,34) suggesting that multiple species with different spin states may be present. Upon drying the sample by azeotropic distillation with toluene the following observations were made: (i) paramagnetic signals develop first at 15 ppm then at 50-60 ppm corresponding to the signals of ␤-pyrrole protons (35)(36)(37)(38) and (ii) the 4 band of a high spin species develops (1,342 cm Ϫ1 ) to give a 3:7 ratio 4 band(HS)/4 band(LS). However, washing a dry sample with water resulted in the disappearance of both the 1 H-NMR paramagnetic signals and the resonance Raman 4 high spin marker band.…”
Section: Resultsmentioning
confidence: 99%
“…1B) [2]. This type of atropisomerism in porphyrins has been utilised in the design of superstructured models of the active sites of hemoproteins [3][4][5][6][7].Porphyrins (see Fig. 3) are macrocycles consisting of four pyrroles linked by four methine bridges.…”
mentioning
confidence: 99%
“…1B) by visual comparison of the areas of the six types of methyl group resonances [11]. According to other studies on porphyrins (see references [3][4][5] and [12][13][14][15][16][17][18][19] for a representative list of examples), the existence of atropisomers is usually revealed in NMR spectroscopy by multiplets with rather broad peaks mainly due to extensive overlap of signals.To clearly illustrate atropisomerism, we discuss the wellresolved 250 MHz 1 H NMR spectrum of meso-tetrakis(3-sulfonatomesityl)porphyrin tetrasodium salt (Fig. 3), a porphyrin prepared (note 1) as a potential antiviral agent [20] Illustrating atropisomerism in the porphyrin series using NMR spectroscopy -the mesityl ring introduced in the meso positions of the porphyrin has methyl substituents in both ortho positions of the phenyl group, which greatly increases the activation energy of the rotation barrier around the C-C bond diminishing the possibility of thermal isomerization [12].…”
mentioning
confidence: 99%
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“…The first is an extension of single-step coupling of benzaldehyde and pyrrole to produce meso-tetraphenylporphyrin (1 2). Aromatic aldehydes with potential amino groups as ortho-substituents are condensed with pyrrole and the protective structures are linked to the amino groups via amide linkages using appropriate acyl chlorides (5,6). In a modification of this method, the protective structures are linked to the aromatic aldehydes at their ortho positions via ester or ether functions, prior to the coupling with pyrrole (7, 9, 10).…”
mentioning
confidence: 99%