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Synthesis and Characterization of Peripherally Functionalized Porphyrazines and Phthalocyanines

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: 31 December 2025 | Viewed by 462

Special Issue Editors


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Guest Editor
Chair and Department of Chemical Technology of Drugs, Poznan University of Medical Sciences, Rokietnicka 3, 60-806 Poznan, Poland
Interests: organic synthesis; electrochemistry; photocatalysis; nanomaterials; sensors; porphyrinoids

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Guest Editor
Chair and Department of Chemical Technology of Drugs, Poznan University of Medical Sciences, Rokietnicka 3, 60-806 Poznan, Poland
Interests: organic chemistry; medicinal chemistry; nanomaterials; photocatalysis; porphyrinoids; titanium oxide

Special Issue Information

Dear Colleagues,

Porphyrazines and phthalocyanines, also known as tetraazaporphyrins, are synthetic members of the porphyrinoid family. They comprise pyrrole or isoindole moieties, respectively, linked by nitrogen bridges in the form of macrocyclic rings, able to bind metal cations at their center. This binding imparts unique physicochemical and electrochemical properties, tunable by substituting the central cation or functionalizing the heteroaromatic rings. Porphyrazines and phthalocyanines feature an extended aromatic system with 18 conjugated π-electrons, contributing to their stability and optical properties, including visible and ultraviolet light absorption. Their ability to absorb light and generate reactive oxygen species through energy transfer mechanisms is leveraged in photodynamic therapy (targeting cancer cells and microorganisms) and in photocatalysis. Additionally, tetraazaporphyrins' ability to emit fluorescence after light irradiation is employed in photodynamic diagnosis. Porphyrazines and phthalocyanines can also catalyze oxidation and reduction reactions, especially when coordinating d-block metal ions like iron and manganese, which enables them to serve as electrocatalysts.

In this Special Issue, entitled “Synthesis and Characterization of Peripherally Functionalized Porphyrazines and Phthalocyanines”, we invite researchers worldwide who contribute to the field and publish studies highlighting the diverse applicability of tetraazaporphyrins.

Dr. Tomasz Koczorowski
Dr. Dariusz T. Mlynarczyk
Guest Editors

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Keywords

  • porphyrazine
  • phthalocyanine
  • organic synthesis
  • photodynamic therapy
  • photodynamic inactivation
  • photocatalysis
  • photodegradation
  • electrocatalysis

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Published Papers (1 paper)

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Research

17 pages, 3345 KiB  
Article
Novel Tetraphenolic Porphyrazine Capable of MRSA Photoeradication
by Wojciech Szczolko, Eunice Zuchowska, Tomasz Koczorowski, Michal Kryjewski, Jolanta Dlugaszewska and Dariusz T. Mlynarczyk
Molecules 2025, 30(15), 3069; https://doi.org/10.3390/molecules30153069 - 22 Jul 2025
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Abstract
This work presents the synthesis, characterization and evaluation of physicochemical and biological properties of two new aminoporphyrazine derivatives bearing magnesium(II) cations in their cores and peripheral pyrrolyl groups. The synthesis was carried out in several stages, using classical methods and the Microwave-Assisted Organic [...] Read more.
This work presents the synthesis, characterization and evaluation of physicochemical and biological properties of two new aminoporphyrazine derivatives bearing magnesium(II) cations in their cores and peripheral pyrrolyl groups. The synthesis was carried out in several stages, using classical methods and the Microwave-Assisted Organic Synthesis (MAOS) approach. The obtained compounds were characterized using spectral techniques: UV-Vis spectrophotometry, mass spectrometry, 1H and 13C NMR spectroscopy. The porphyrazine derivatives were tested for their electrochemical properties (CV and DPV), which revealed four redox processes, of which in compound 7 positive shifts of oxidation potentials were observed, resulting from the presence of free phenolic hydroxyl groups. In spectroelectrochemical measurements, changes in UV-Vis spectra associated with the formation of positive-charged states were noted. Photophysical studies revealed the presence of characteristic absorption Q and Soret bands, low fluorescence quantum yields and small Stokes shifts. The efficiency of singlet oxygen generation (ΦΔ) was higher for compound 6 (up to 0.06), but compound 7, despite its lower efficiency (0.02), was distinguished by a better biological activity profile. Toxicity tests using the Aliivibrio fischeri bacteria indicated the lower toxicity of 7 compared to 6. The most promising result was the strong photodynamic activity of porphyrazine 7 against the Methicillin-resistant Stapylococcus aureus (MRSA) strain, leading to a more-than-5.6-log decrease in viable counts after the colony forming units (CFU) after light irradiation. Compound 6 did not show any significant antibacterial activity. The obtained data indicate that porphyrazine 7 is a promising candidate for applications in photodynamic therapy of bacterial infections. Full article
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