Bis(dimethylamino)porphyrazines: Synthetic, structural, and spectroscopic investigations

Antonio Garrido Montalban, Wade Jarrell, Eric Riguet, Quentin J. McCubbin, Mairin E. Anderson, Andrew J.P. White, David J. Williams, Anthony G.M. Barrett*, Brian M. Huffman

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

52 Scopus citations

Abstract

The synthesis and isolation of unsymmetrical porphyrazines bearing two, four, and six bis(dimethylamino) functionalities has been achieved via the base-catalyzed cross-condensation of 1,2-dicyanobenzene 8 and bis(dimethylamino)maleonitrile 7. In addition, the benzo-fused hexaaminoporphyrazine dimer 10 was prepared from condensation of dinitrile 7 (in excess) with benzenebis(1,3-diiminopyrroline) 9. Electrochemical studies reveal that all porphyrazines may be readily oxidized. The X-ray structures of porphyrazines 2b and 5a and the cis isomer 3a are presented. The latter is the first structure of a porphyrazine having a cis-type substitution pattern. The extended π-conjugation in dimer 10 causes a ~100 nm red-shifted Q-band in the electronic absorption spectrum.

Original languageEnglish (US)
Pages (from-to)2472-2478
Number of pages7
JournalJournal of Organic Chemistry
Volume65
Issue number8
DOIs
StatePublished - Apr 21 2000

ASJC Scopus subject areas

  • Organic Chemistry

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