Seco-Porphyrazines: Synthetic, Structural, and Spectroscopic Investigations

Autor:	Brian M. Hoffman, Andrew J. P. White, Antonio Garrido Montalban, Neelakandha S. Mani, Steven J. Lange, Anthony G. M. Barrett, L. Scott Beall, David J. Williams
Rok vydání:	1997
Předmět:	Absorption spectroscopy Organic Chemistry chemistry.chemical_element Free base Porphyrazine Zinc Ring (chemistry) Photochemistry chemistry.chemical_compound Crystallography chemistry Amide Molecule Pyrrole
Zdroj:	The Journal of Organic Chemistry. 62:9284-9289
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo971599x
Popis:	Linstead macrocyclization of dinitrile 1 gave [octakis(dimethylamino)porphyrazinato]magnesium(II) 2 and the seco-porphyrazine 4 from adventitious oxidation. The structure of the latter has been unequivocally established by an X-ray crystallographic study. Alternatively, compound 4 was obtained in high yield from the manganese dioxide-mediated oxidation of the free base porphyrazine 3. This convenient method was further extended to core metalated and unsymmetrical porphyrazines. In crystals of zinc−seco-porphyrazine 11, the molecules exist as face-to-face dimers linked via complexation of the zinc center in one molecule to one of the amide oxygen atoms in the other and vice versa. The cleaved pyrrole ring in seco- and diseco-porphyrazines causes a ∼50−70 nm red-shifted split Q-band in the electronic absorption spectra.
Databáze:	OpenAIRE
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