Tetrapyrazinoporphyrazine with eight peripheral adamantanylsulfanyl units – Synthesis and physicochemical study

[Display omitted] •Zinc (1-adamantylsulfanyl)-octasubstituted tetrapyrazinoporphyrazine was obtained.•X-ray structures of precursor pyrazine derivatives are discussed.•Singlet oxygen generation and fluorescence properties were assessed.•Electrochemical studies revealed two reduction and one oxidatio...

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Bibliographic Details
Published in:Synthetic metals 2018-10, Vol.244, p.66-72
Main Authors: Tillo, Adam, Kryjewski, Michal, Bendzińska-Berus, Wioletta, Langer, Dominik, Rebis, Tomasz, Popenda, Lukasz, Jurga, Stefan, Mielcarek, Jadwiga, Goslinski, Tomasz, Tykarska, Ewa
Format: Article
Language:English
Subjects:
Adamantane
Chemical compounds
Chemical synthesis
Crystal structure
Crystallography
Electrochemistry
Fluorescence
Macrocyclic compounds
Organic chemistry
Oxidation
Oxygen
Physical properties
Porphyrazine
Singlet oxygen
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Summary:[Display omitted] •Zinc (1-adamantylsulfanyl)-octasubstituted tetrapyrazinoporphyrazine was obtained.•X-ray structures of precursor pyrazine derivatives are discussed.•Singlet oxygen generation and fluorescence properties were assessed.•Electrochemical studies revealed two reduction and one oxidation processes. A novel, (1-adamantylsulfanyl)-octasubstituted tetrapyrazinoporphyrazine has been synthesized and analyzed for its key physicochemical properties. Also, two 1-adamantylsulfanyl-substituted pyrazine derivatives were compared, and their crystallographic structures as well as chemical reactivity were assessed and discussed. Porphyrazine macrocycle showed good fluorescence and singlet oxygen generation properties as well as photostability. In addition, studied adamantylsulfanyl porphyrazine, despite its hydrophobic nature, revealed good solubility in polar solvents. Electrochemical studies revealed that the macrocycle underwent oxidation by one one-electron process and reduction with two one-electron processes.
ISSN:0379-6779
1879-3290
DOI:10.1016/j.synthmet.2018.07.002