Novel peripherally functionalized seco-porphyrazines: Synthesis, characterization and spectroscopic evaluation

Efstathia G. Sakellariou, Antonio Garrido Montalban, Scott L. Beall, David Henderson, Hubert G. Meunier, David Phillips, Klaus Suhling, Anthony G.M. Barrett*, Brian M. Hoffman

*Corresponding author for this work

Research output: Contribution to journalArticle

37 Scopus citations

Abstract

Co-macrocyclizations of 2,3-dipropylmaleonitrile and 2,3-di-(4- (methoxycarbonyl)phenyl)maleonitrile, respectively, with N,N′-dibenzyl-N, N′-di-(11-tetrahydropyranyloxy-3,6,9-trioxo-undecyl))maleonitrile and N,N,N′,N′-tetramethylmaleonitrile were used to prepare derivatives of the 4,5-diamino-porphyrazine systems including the zinc(II) complexes. Subsequent oxidation of the macrocycles with potassium permanganate gave the corresponding seco-porphyrazines. These were shown to be efficient sensitizers for the production of singlet oxygen (ΦΔ=0.15-0.57) by the determination of their photophysical properties.

Original languageEnglish (US)
Pages (from-to)9083-9090
Number of pages8
JournalTetrahedron
Volume59
Issue number46
DOIs
StatePublished - Nov 10 2003

Keywords

  • Linstead macrocyclization
  • Porphyrazine
  • Sensitization
  • Singlet oxygen

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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