Tetrapyrazinoporphyrazine with eight peripheral adamantanylsulfanyl units – Synthesis and physicochemical study

Publish Year: 2018
Publisher:  Synthetic Metals, 2018, 244, 66-72
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A. Tillo, M. Kryjewski, W. Bendzińska-Berus, D. Langer, T. Rebis, Ł. Popenda, S. Jurga, J. Mielcarek, T. Goslinski, E. Tykarskaa
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.

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