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Octakis(2-pyridyl)porphyrazine and Its Neutral Metal Derivatives: UV-Visible Spectral, Electrochemical, and Photoactivity Studies

Sciscione, F; Cong, L; Donzello, MP; Viola, E; Ercolani, C; Kadish, KM; (2017) Octakis(2-pyridyl)porphyrazine and Its Neutral Metal Derivatives: UV-Visible Spectral, Electrochemical, and Photoactivity Studies. Inorganic Chemistry , 56 (10) pp. 5813-5826. 10.1021/acs.inorgchem.7b00418. Green open access

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Abstract

Tetrapyrrolic porphyrazine macrocycles with externally appended 2-pyridyl rings were synthesized and characterized as to their spectroscopic, electrochemical, and photophysical properties. The investigated compounds are represented as [Py8PzH2], the unmetalated octakis(2-pyridyl)porphyrazine, and the metal complexes [Py8PzM], where M is MgII(H2O), CuII, ZnII, or CoII. The spectroscopic properties and the electrochemical behavior of these compounds were examined in solution of polar (pyridine, dimethyl sulfoxide, and dimethylformamide) and nondonor solvents (CHCl3, CH2Cl2), and the data were compared with those obtained from earlier studies on the related tetrapyrazinoporphyrazines, [Py8TPyzPzM], and the tetraquinoxalinoporphyrazines, [Py8QxPzM], also bearing externally 2-pyridyl rings, and characterized by a more extended central π-conjugated macrocyclic framework. The newly synthesized porphyrazines possess good solubility and are present in their monomeric form in all the examined solvents as shown by UV–visible spectra. The unmetalated species and metal derivatives undergo multiple one-electron reductions within the potential range of the nonaqueous examined solvents. The derivatives with nonredox active metal centers could accept four electrons on the conjugated macrocycle, while the CoII complex was characterized by a single one-electron oxidation and five reductions in DMSO. The photosensitizer activity for the generation of singlet oxygen was also examined for the MgII(H2O) and ZnII complexes in DMF, with measured ΦΔ values being, respectively, 0.42 and 0.64, this latter value indicating the ZnII species as being a promising material for use as anticancer agent in photodynamic therapy.

Type: Article
Title: Octakis(2-pyridyl)porphyrazine and Its Neutral Metal Derivatives: UV-Visible Spectral, Electrochemical, and Photoactivity Studies
Open access status: An open access version is available from UCL Discovery
DOI: 10.1021/acs.inorgchem.7b00418
Publisher version: http://dx.doi.org/10.1021/acs.inorgchem.7b00418
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
Keywords: Science & Technology, Physical Sciences, Chemistry, Inorganic & Nuclear, Chemistry, Appended Pyridine Rings, Electron-Deficient Properties, Singlet Oxygen Production, Photophysical Properties, Photodynamic Therapy, CU-II, ZN-II, Anticancer Agents, Quantum Yields, CD-II
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10046654
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