Tetrapyrazinoporphyrazine with eight peripheral adamantanylsulfanyl units – Synthesis and physicochemical study

• Published in: Synthetic metals Vol. 244; pp. 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: Journal Article
• Language: English
• Published: Lausanne Elsevier B.V 01.10.2018; Elsevier BV
• Subjects: Adamantane; Chemical compounds; Chemical synthesis; Crystal structure; Crystallography; Electrochemistry; Fluorescence; Macrocyclic compounds; Organic chemistry; Oxidation; Oxygen; Physical properties; Porphyrazine; Singlet oxygen; Electrochemistry; Singlet oxygen; Adamantane; Porphyrazine; Crystal structure
• ISSN: 0379-6779; 1879-3290
• DOI: 10.1016/j.synthmet.2018.07.002

[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.