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In two steps from simple meso-tetraphenylporphyrin to its derivatives exhaustively β-substituted at the ‘Eastern half’

Agnieszka Mikus 1
Agnieszka Mikus
1 Faculty of Chemistry, Warsaw University of Technology, Warsaw, Poland
10.1016/j.mencom.2024.01.021
Published 2023-12-25
Communication , Volume 34, Issue 1, 70-73
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Mikus A. In two steps from simple meso-tetraphenylporphyrin to its derivatives exhaustively β-substituted at the ‘Eastern half’ // Mendeleev Communications. 2023. Vol. 34. No. 1. pp. 70-73.
GOST all authors (up to 50) Copy
Mikus A. In two steps from simple meso-tetraphenylporphyrin to its derivatives exhaustively β-substituted at the ‘Eastern half’ // Mendeleev Communications. 2023. Vol. 34. No. 1. pp. 70-73.
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TY - JOUR
DO - 10.1016/j.mencom.2024.01.021
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.01.021
TI - In two steps from simple meso-tetraphenylporphyrin to its derivatives exhaustively β-substituted at the ‘Eastern half’
T2 - Mendeleev Communications
AU - Mikus, Agnieszka
PY - 2023
DA - 2023/12/25
PB - Mendeleev Communications
SP - 70-73
IS - 1
VL - 34
ER -
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@article{2023_Mikus,
author = {Agnieszka Mikus},
title = {In two steps from simple meso-tetraphenylporphyrin to its derivatives exhaustively β-substituted at the ‘Eastern half’},
journal = {Mendeleev Communications},
year = {2023},
volume = {34},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.01.021},
number = {1},
pages = {70--73},
doi = {10.1016/j.mencom.2024.01.021}
}
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Mikus, Agnieszka. “In two steps from simple meso-tetraphenylporphyrin to its derivatives exhaustively β-substituted at the ‘Eastern half’.” Mendeleev Communications, vol. 34, no. 1, Dec. 2023, pp. 70-73. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.01.021.
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Keywords

carbanions
nitro group
photodynamic therapy (PDT)
photosensitizers
porphyrin complexes
vicarious nucleophilic substitution
β-derivatization

Abstract

The two-step synthesis of porphyrin derivatives, exhaustively bbb-substituted at the ‘Eastern half’, starting from meso- tetraarylporphyrin chelates (Cuii, Znii, Niii) upon their reaction with nitric acid, is described. The intermediates obtained (mainly dinitro-derivatives) in the reaction with carbanions bearing a leaving group X at the reactive centre give tetrasubstituted at the bbb-positions products, the ones of vicarious nucleophilic substitution of hydrogen. The products seem to be potential anticancer PDT agents, practically unavailable by other methods.

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