Seco-Porphyrazines: Synthetic, Structural, and Spectroscopic Investigations

Antonio Garrido Montalban*, Steven J. Lange, L. Scott Beall, Neelakandha S. Mani, David J. Williams, Andrew J.P. White, Anthony G.M. Barrett, Brian M Hoffman

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

68 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)9284-9289
Number of pages6
JournalJournal of Organic Chemistry
Volume62
Issue number26
DOIs
StatePublished - Jan 1 1997

ASJC Scopus subject areas

  • Organic Chemistry

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