3,4‐Diethylpyrrole and 2,3,7,8,12,13,17,18‐Octaethylporphyrin

Sessler, Jonathan L.; Mozaffari, Azadeh; Johnson, Martin R.

doi:10.1002/0471264180.os070.09

Cited by 54 publications

(64 citation statements)

References 17 publications

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“…This afforded the diol 13 as an unstable solid after a non-acidic aqueous workup. [27] Treating diol 13 with ten equivalents of 3,4-diethylpyrrole (14) [28] and a catalytic amount of TFA in anhydrous CH 2 Cl 2 for 1 h, followed by neutralization with Et 3 N, gave the functionalized MPTTF 15 as a yellow oil in 65 % yield after column chromatography. This compound was used without any further purification.…”

Section: Full Papermentioning

confidence: 99%

Tetrathiafulvalene Porphyrins

Nielsen

Levillain

Lynch

et al. 2008

Chemistry A European J

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Four tetrathiafulvalene (TTF)-annulated porphyrins 1-4 were synthesized and characterized. All contain a tetraphenylporphyrin (TPP) core onto which four, two, or one TTF subunits were annulated. Absorption and fluorescence spectroscopic studies together with electrochemical investigations reveal that interactions between the porphyrin system and the annulated TTF units take place in solution. The annulation of one or more TTF units to the porphyrin core has a profound effect on the reduction potentials associated with this latter framework, with positive shifts in the range of 0.105 to 0.355 V and 0.200 to 0.370 V for the first and second reduction potential, respectively, compared to the corresponding processes in the model compound TPP, 18. The redox potentials for the first oxidation of the TTF units are considerably shifted in 4 (DeltaE(ox)(1)=+0.285 V) and 2 (DeltaE(ox)(1)=-0.140 V), whereas for 1 and 3 these potentials remain within the region expected for a normal TTF unit. Considerable changes in the second oxidation potential associated with the TTF subunits were seen for 2 (DeltaE(ox)(1)=-0.085) and 3 (DeltaE(ox)(1)=-0.175). The emission spectra of 1-4 revealed that the porphyrin fluorescence is almost quenched in the neutral state of the TTF-annulated porphyrins, a finding that is consistent with substantial electron transfer taking place from the TTF subunits to the porphyrin core. Oxidation of the TTF unit(s) (TTF-->TTF(*+)) present in 1-4 leads to the emission intensity being restored.

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Section: Full Papermentioning

confidence: 99%

Tetrathiafulvalene Porphyrins

Nielsen

Levillain

Lynch

et al. 2008

Chemistry A European J

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“…Chemical shifts δ are quoted in parts per million (ppm) downfield New N-Substituted Hydrazones of Ni(II) Complexes by monopyrrole condensation described by Johnson. [19] Ni(II) complexes of coproporphyrin I tetraethyl ester and β-octaethylporphyrin were prepared according to procedure described by K. Smith. [20] A typical procedure for synthesis of Ni(II) formyl derivatives of porphyrins.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Study of New N-Substituted Hydrazones of Ni(II) Complexes of β-Octaethylporphyrin and Coproporphyrin I Tetraethyl Ester

Shkirdova¹,

Zamilatskov²,

Stanetskaya³

et al. 2017

MHC

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N-Substituted hydrazones of nickel complexes of β-octaethylporphyrin and tetraethyl ester of coproporphyrin I were obtained. These compounds can serve as intermediate compounds for the preparation of meso-functionalized derivatives of porphyrins by means of various reactions. In the first stage Vilsmeier-Haack reaction was carried out by the interaction of nickel complexes of β-octaethylporphyrin and tetraethyl ester of coproporphyrin I with N,N-dimethylformamide and phosphorus(V) oxochloride forming the so-called "phosphorus complex", which was hydrolyzed with saturated solution of sodium acetate. The corresponding meso-formyl derivatives of metal porphyrins were obtained as a result. Synthesis of the hydrazones was carried out by the reactions of meso-formyl derivatives with the hydrazines using trifluoroacetic acid as a catalyst. The result of the reaction was formation of hydrazones in the form of a mixture of E-and Z-isomers, which were separated using preparative thin layer chromatography. Thus a series of hydrazoneswith different substituents at the nitrogen atom was obtained. The structures of all obtained compounds were determined using the methods of NMR spectroscopy, electronic absorption spectroscopy and mass spectrometry. For nickel complex of tosylhydrazone derivative of β-octaethylporphyrin the crystal structure was determined using X-ray diffraction. X-ray analysis shows that porphyrin molecules in the crystal form dimers bonded by two hydrogen bonds between the hydrogen atom of the NH-group of hydrazone and the oxygen atom of the sulfonate groups.

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“…The largely neglected Piloty-Robinson [720][721][722] pyrrole synthesis has been adapted to microwave conditions [723], providing a route to 3,4-dialkylpyrroles, in particular 3,4-diethylpyrrole, a building block for construction of octaethylporpyrins [724,725]. Thus, the intermediate azine 474 was generated by exposure of butyraldehyde to hydrazine hydrate in diethyl ether.…”

Section: Addendummentioning

confidence: 99%