Synthesis of porphyrazine-octaamine, hexamine and diamine derivatives

Matthew J. Fuchter, L. Scott Beall, Sven M. Baum, Antonio Garrido Montalban, Efstathia G. Sakellariou, Neelakandha S. Mani, Todd Miller, Benjamin J. Vesper, Andrew J.P. White, David J. Williams, Anthony G.M. Barrett*, Brian M. Hoffman

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

42 Scopus citations

Abstract

The syntheses of a variety of substituted diaminomaleonitriles, with variable nitrogen substituents, were undertaken. Linstead macrocyclization of the resulting diaminomaleonitriles gave access to a wide range of functionalized porphyrazine-octaamines and hexamines and norphthalocyaninediamines. Conversion of these macrocycles into metallic derivatives and studies of their electronic absorption, solubility and electrochemistry are described. These flexible tetraazaporphyrins show potential in a range of applications including biomedical agents, novel charge-transfer complexes, chemical sensors, novel electronic materials and non-linear optics.

Original languageEnglish (US)
Pages (from-to)6115-6130
Number of pages16
JournalTetrahedron
Volume61
Issue number25
DOIs
StatePublished - Jun 20 2005

Keywords

  • Aminoporphyrazine
  • Electrochemistry
  • Linstead macrocyclization
  • Nickel porphyrazines
  • Porphyrazine
  • UV-vis spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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