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

Valeriia D. Andreeva,^a Gelii V. Ponomarev,^b Alena O. Shkirdova,^a Vladimir S. Tyurin,^a@1 and Ilya A. Zamilatskov^a,^c@2

^aA.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 119071 Moscow, Russian Federation
^bOrekhovich Institute of Biomedical Chemistry, 119121 Moscow, Russian Federation
^cA.N. Kosygin Russian State University, Department of Organic Chemistry, 119071 Moscow, Russian Federation
^@1Corresponding author E-mail: vst-1970@mail.ru
^@2Corresponding author E-mail: joz@mail.ru

DOI: 10.6060/mhc213990z
Macroheterocycles 2021 14(4) 263-269

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

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