Porphyrazines with annulated diazepine rings. 6. Synthesis and properties of the alkyl substituted derivative - MgII complex of tetrakis-2,3-(5,7-di-tert-butyl-6H-1,4-diazepino)porphyrazine
| Autor: | Ekaterina N. Tarakanova, Pavel A. Stuzhin, Sergey E. Nefedov, Pavel A. Tarakanov, Roman S. Kumeev |
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| Rok vydání: | 2021 |
| Předmět: | |
| Zdroj: | Journal of Porphyrins and Phthalocyanines. 25:1203-1211 |
| ISSN: | 1099-1409 1088-4246 |
| DOI: | 10.1142/s1088424621501212 |
| Popis: | Novel MgII porphyrazine 3 bearing four appended seven-membered tert-butyl substituted 1,4-diazepine rings was prepared via Linstead macrocyclization of 5,7-di-tert-butyl-6[Formula: see text]-1,4-diazepine-2,3-dicarbonitrile 2, obtained by condensation of diaminomaleonitrile and 2,2,6,6-tetramethylheptanedione-3,5 (1) in anhydrous ethanol in the presence of P2O5. The structure of the dinitrile precursor 2 was established by single crystal X-ray work. 1H NMR study revealed that the 1,4-diazepine ring is present in the 6[Formula: see text] tautomeric form both in the dinitrile precursor 2 and the MgII complex 3. The inversion of the tert-butyl substituted diazepine ring occurs more easily than in the case of aryl and alkenyl substituted species. Although porphyrazine 3exhibit some tendency to aggregation in low-polar solvents the presence of bulky tert-butyl substituents stabilizes the monomeric form and hinders formation of H-bonded dimers characteristic for aryl and styryl substituted analogues. |
| Databáze: | OpenAIRE |
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