Isomers of β , β -Dinitro-5,10,15,20-tetraphenylporphy-rin Derivatives: Valuable Starting Materials for Further Transformations

The synthesis, chromatographic isolation, and structure elucidation of , -substituted isomers of dinitro-5,10,15,20-tetraphenylporphyrin complexes are described. -Tetraphenyl-porphyrin chelates (Cu , Ni , Co ) upon reaction wit e.g., itric acid (yellow HNO₃, = 1.52, diluted to 25⁻50%) in CHCl₃ forme...

Full description

Saved in:
Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2019-02, Vol.24 (5), p.838
Main Authors: Mikus, Agnieszka, Rosa, Mariusz, Ostrowski, Stanisław
Format: Article
Language:English
Subjects:
2D NMR
complexes
electrophilic substitution
nitric acid
porphyrins
β-nitration
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The synthesis, chromatographic isolation, and structure elucidation of , -substituted isomers of dinitro-5,10,15,20-tetraphenylporphyrin complexes are described. -Tetraphenyl-porphyrin chelates (Cu , Ni , Co ) upon reaction wit e.g., itric acid (yellow HNO₃, = 1.52, diluted to 25⁻50%) in CHCl₃ formed a mixture of nitro-derivatives with combined yields of 80%. This nitration (under optimized conditions: 25⁻30% HNO₃, 30⁻40 min, r.t.) can be carried out selectively to give mainly , -dinitro-compounds in yields of up to 73%. From the above mixtures of five possible regioisomers that can be formed, usually two or three of them were isolated, for which the structures were assigned on the basis of ¹H NMR spectra including COSY and NOESY measure-ments. These types of products are attractive starting materials for synthesis of potential anticancer PDT agents with unique structures, being practically unavailable by any other alternative method.
ISSN:1420-3049
DOI:10.3390/molecules24050838