Palladium Complexes of Azomethine Derivatives of Porphyrins as Potential Photosensitizers

Tyurin, V. S.; Erzina, Dina R.; Zamilatskov, Ilya A.; Chernyadyev, Andrey Yu.; Ponomarev, G. V.; Yashunskiy, D.V.; Maksimova, A.V.; Krasnovskiy, A. A.; Tsivadze, A. Yu.

doi:10.6060/mhc151199z

Cited by 10 publications

(6 citation statements)

References 17 publications

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“…The iminium group of the phosphorus complex is more active to nucleophilic attack compared to the formyl group. Azomethine derivatives of nickel and palladium complexes of various porphyrinoids, including OEP, tetraalkyl esters of coproporphyrins I and II, mesoporphyrin IX, and mesochlorin e6, were obtained by direct interaction of "phosphorus complexes" with amines (Scheme 7) [33][34][35].…”

Section: Reactions Of Meso-formylporphyrins With Nitrogen Nucleophilesmentioning

confidence: 99%

Meso-Formyl, Vinyl, and Ethynyl Porphyrins—Multipotent Synthons for Obtaining a Diverse Array of Functional Derivatives

Tyurin,

Shkirdova,

Koifman

et al. 2023

Molecules

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This review presents a strategy for obtaining various functional derivatives of tetrapyrrole compounds based on transformations of unsaturated carbon-oxygen and carbon-carbon bonds of the substituents at the meso position (meso-formyl, vinyl, and ethynyl porphyrins). First, synthetic approaches to the preparation of these precursors are described. Then diverse pathways for the transformations of the multipotent synthons are discussed, revealing a variety of products of such reactions. The structures, electronic, and optical properties of the compounds obtained by the methods under consideration are analyzed. In addition, there is an overview of the applications of the products obtained. Biomedical use of the compounds is among the most important. Finally, the advantages of using the reviewed synthetic strategy to obtain dyes with targeted properties are highlighted.

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Section: Reactions Of Meso-formylporphyrins With Nitrogen Nucleophilesmentioning

confidence: 99%

Meso-Formyl, Vinyl, and Ethynyl Porphyrins—Multipotent Synthons for Obtaining a Diverse Array of Functional Derivatives

Tyurin,

Shkirdova,

Koifman

et al. 2023

Molecules

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“…[39] The trifluoroacylated amino derivative 5 was used as a starting material for the electron acceptor fragment insertion as the trifluoroacyl played a role of a protective group for the reactive amino group. The Vilsmeier-Haack formylation of 5 with POCl 3 /DMF [39][40][41] was initially performed, and the so called intermediate "phosphorus complex" was then subjected to the reaction with hydrazine leading to the hydrazone, which was used in the next step without isolation. Finally, p-nitrobenzaldehyde was added to the reaction mixture containing the hydrazone and the condensation products of the three stage reaction were isolated.…”

Section: Synthesis Of Azinesmentioning

confidence: 99%

Modification of β-Octaethylporphyrin via Insertion of Amino and Azino Groups into meso-Positions

Andreeva,

Ponomarev,

Shkirdova

et al. 2021

MHC

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The functionalization of Ni(II) β-octaethylporphyrin was performed by introducing various amino and azino groups into meso-positions. Amino, n-propylamino, and trifluoromethylacetylamino groups were used as electron donor substituents, while azino group was inserted as an electron acceptor. The azine fragment was inserted through formylation followed by reaction with hydrazine and then with aromatic aldehydes, and the corresponding azine derivatives of p-nitrophenylbenzaldehyde and methyl pyropheophorbide d were obtained. It was found that under the conditions of formylation of meso-(trifluoroacetamido)-β-octaethylporphyrin, the amide fragment was oxidized to form hydroxamic acid. As a result of substitution of meso-positions of β-octaethylporphyrin, new functionalized porphyrin derivatives with significantly altered electron-optical properties were obtained. In particular, the azine bridged conjugate of β-octaethylporphyrin with methyl pyropheophorbide d was synthesized, the electronic absorption spectrum of which contains bathochromically shifted long-wavelength bands. The resulting compounds could be of interest as potential photosensitizers, sensor dyes and biologically active compounds.

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“…The potential use of derivatives of coproporphyrins as multiparametric sensors for oxygen and H + is one of the main factors driving a growing interest in the synthesis of new porphyrin derivatives (Borchert et al, 2011). Recently, we reported synthetic and crystallographic studies of the coproporphyrin I molecular complexes with Pd II (Volov et al, 2014;Tyurin et al, 2015). We report herein the synthesis and structural characterization of the novel ruthenium(II) complex of coproporphyrin I tetraethyl ester, (1), namely catena-poly [[carbonylruthenium(II)…”

Section: Introductionmentioning

confidence: 99%

Polymeric structure of a coproporphyrin I ruthenium(II) complex: a powder diffraction study

Andreev

Zverev²,

Zamilatskov³

et al. 2017

Acta Crystallogr C Struct Chem

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Porphyrin complexes of ruthenium are widely used as models for the heme protein system, for modelling naturally occurring iron-porphyrin systems and as catalysts in epoxidation reactions. The structural diversity of ruthenium complexes offers an opportunity to use them in the design of multifunctional supramolecular assemblies. Coproporphyrins and metallocoproporphyrins are used as sensors in bioassay and the potential use of derivatives as multiparametric sensors for oxygen and H is one of the main factors driving a growing interest in the synthesis of new porphyrin derivatives. In the coproporphyrin I Ru complex catena-poly[[carbonylruthenium(II)]-μ-2,7,12,17-tetrakis[2-(ethoxycarbonyl)ethyl]-3,8,13,18-tetramethylporphyrinato-κN,N',N'',N''':O], [Ru(CHNO)(CO)], the Ru centre is coordinated by four N atoms in the basal plane, and by axial C (carbonyl ligand) and O (ethoxycarbonylethyl arm from a neighbouring complex) atoms. The complex adopts a distorted octahedral geometry. Self-assembly of the molecules during crystallization from a methylene chloride-ethanol (1:10 v/v) solution at room temperature gives one-dimensional polymeric chains.

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Palladium Complexes of Azomethine Derivatives of Porphyrins as Potential Photosensitizers

Abstract: Various isomers of azomethine derivatives of mesoporphyrin IX were first obtained in the form of palladium complexes by the interaction of the so-called "phosphorus complex", produced in situ in the Vilsmeier

Cited by 10 publications

References 17 publications

Meso-Formyl, Vinyl, and Ethynyl Porphyrins—Multipotent Synthons for Obtaining a Diverse Array of Functional Derivatives

Meso-Formyl, Vinyl, and Ethynyl Porphyrins—Multipotent Synthons for Obtaining a Diverse Array of Functional Derivatives

Modification of β-Octaethylporphyrin via Insertion of Amino and Azino Groups into meso-Positions

Polymeric structure of a coproporphyrin I ruthenium(II) complex: a powder diffraction study

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