Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents
Ferrocene is useful in modern organometallic chemistry due to its versatile applications in material sciences, catalysis, medicinal chemistry, and diagnostic applications. The ferrocene moiety can potentially serve many purposes in therapeutics and diagnostics. In the course of this study, (6-bromo-...
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MDPI AG
2023-07-01
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| author | Mina Hassani Amanda Leda Weronika Porolnik Michal Falkowski Tomasz Rębiś Jaroslaw Piskorz Lukasz Popenda Michal Wicinski Dariusz T. Mlynarczyk Nejat Düzgüneş Michal P. Marszall |
| author_facet | Mina Hassani Amanda Leda Weronika Porolnik Michal Falkowski Tomasz Rębiś Jaroslaw Piskorz Lukasz Popenda Michal Wicinski Dariusz T. Mlynarczyk Nejat Düzgüneş Michal P. Marszall |
| author_sort | Mina Hassani |
| collection | DOAJ |
| description | Ferrocene is useful in modern organometallic chemistry due to its versatile applications in material sciences, catalysis, medicinal chemistry, and diagnostic applications. The ferrocene moiety can potentially serve many purposes in therapeutics and diagnostics. In the course of this study, (6-bromo-1-oxohexyl)ferrocene was combined with dimercaptomaleonitrile sodium salt to yield a novel maleonitrile derivative. Subsequently, this compound was subjected to an autocyclotetramerization reaction using the Linstead conditions in order to obtain an octaferrocenyl-substituted magnesium(II) sulfanyl porphyrazine. Following that, both compounds—the maleonitrile derivative and the porphyrazine derivative—were subjected to physicochemical characterization using UV-Vis, ES-TOF, MALDI-TOF, and one-dimensional and two-dimensional NMR spectroscopy. Moreover, the sulfanyl porphyrazine was subjected to various photophysical studies, including optical absorption and emission measurements, as well as the evaluation of its photochemical properties. Values of singlet oxygen generation quantum yields were obtained in different organic solvents. The electrochemical properties of the synthesized compounds were studied using cyclic voltammetry. According to the electrochemical results, the presence of electron-withdrawing oxohexyl groups attached to ferrocene afforded significantly more positive oxidation potentials of the ferrocene-based redox process up to 0.34 V vs. Fc<sup>+</sup>/Fc. |
| first_indexed | 2024-03-11T01:33:21Z |
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| id | doaj.art-86001f43b38c42b58fec65ff22b0cb4c |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T01:33:21Z |
| publishDate | 2023-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-86001f43b38c42b58fec65ff22b0cb4c2023-11-18T17:09:54ZengMDPI AGMolecules1420-30492023-07-012813521510.3390/molecules28135215Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl SubstituentsMina Hassani0Amanda Leda1Weronika Porolnik2Michal Falkowski3Tomasz Rębiś4Jaroslaw Piskorz5Lukasz Popenda6Michal Wicinski7Dariusz T. Mlynarczyk8Nejat Düzgüneş9Michal P. Marszall10Department of Medicinal Chemistry, Collegium Medicum in Bydgoszcz, Faculty of Pharmacy, Nicolaus Copernicus University in Torun, A. Jurasza 2, 85-089 Bydgoszcz, PolandInstitute of Chemistry and Technical Electrochemistry, Poznan University of Technology, Berdychowo 4, 60-965 Poznan, PolandChair and Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Rokietnicka 3, 60-806 Poznan, PolandDepartment of Medicinal Chemistry, Collegium Medicum in Bydgoszcz, Faculty of Pharmacy, Nicolaus Copernicus University in Torun, A. Jurasza 2, 85-089 Bydgoszcz, PolandInstitute of Chemistry and Technical Electrochemistry, Poznan University of Technology, Berdychowo 4, 60-965 Poznan, PolandChair and Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Rokietnicka 3, 60-806 Poznan, PolandNanoBioMedical Centre, Adam Mickiewicz University, Wszechnicy Piastowskiej 3, 61-614 Poznan, PolandDepartment of Pharmacology and Therapy, Collegium Medicum in Bydgoszcz, Faculty of Medicine, Nicolaus Copernicus University in Torun, Curie Sklodowskiej 9, 85-094 Bydgoszcz, PolandChair and Department of Chemical Technology of Drugs, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, PolandDepartment of Biomedical Sciences, Arthur A. Dugoni School of Dentistry, University of the Pacific, San Francisco, CA 94103, USADepartment of Medicinal Chemistry, Collegium Medicum in Bydgoszcz, Faculty of Pharmacy, Nicolaus Copernicus University in Torun, A. Jurasza 2, 85-089 Bydgoszcz, PolandFerrocene is useful in modern organometallic chemistry due to its versatile applications in material sciences, catalysis, medicinal chemistry, and diagnostic applications. The ferrocene moiety can potentially serve many purposes in therapeutics and diagnostics. In the course of this study, (6-bromo-1-oxohexyl)ferrocene was combined with dimercaptomaleonitrile sodium salt to yield a novel maleonitrile derivative. Subsequently, this compound was subjected to an autocyclotetramerization reaction using the Linstead conditions in order to obtain an octaferrocenyl-substituted magnesium(II) sulfanyl porphyrazine. Following that, both compounds—the maleonitrile derivative and the porphyrazine derivative—were subjected to physicochemical characterization using UV-Vis, ES-TOF, MALDI-TOF, and one-dimensional and two-dimensional NMR spectroscopy. Moreover, the sulfanyl porphyrazine was subjected to various photophysical studies, including optical absorption and emission measurements, as well as the evaluation of its photochemical properties. Values of singlet oxygen generation quantum yields were obtained in different organic solvents. The electrochemical properties of the synthesized compounds were studied using cyclic voltammetry. According to the electrochemical results, the presence of electron-withdrawing oxohexyl groups attached to ferrocene afforded significantly more positive oxidation potentials of the ferrocene-based redox process up to 0.34 V vs. Fc<sup>+</sup>/Fc.https://www.mdpi.com/1420-3049/28/13/5215ferrocenesinglet oxygenporphyrazinevoltammetrymacrocyclic compound |
| spellingShingle | Mina Hassani Amanda Leda Weronika Porolnik Michal Falkowski Tomasz Rębiś Jaroslaw Piskorz Lukasz Popenda Michal Wicinski Dariusz T. Mlynarczyk Nejat Düzgüneş Michal P. Marszall Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents Molecules ferrocene singlet oxygen porphyrazine voltammetry macrocyclic compound |
| title | Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents |
| title_full | Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents |
| title_fullStr | Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents |
| title_full_unstemmed | Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents |
| title_short | Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents |
| title_sort | synthesis electrochemical and photochemical properties of sulfanyl porphyrazine with ferrocenyl substituents |
| topic | ferrocene singlet oxygen porphyrazine voltammetry macrocyclic compound |
| url | https://www.mdpi.com/1420-3049/28/13/5215 |
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