title: Bis(dimethylamino)porphyrazines: synthetic, structural, and spectroscopic investigations.
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 pi-conjugation in dimer 10 causes a approximately 100 nm red-shifted Q-band in the electronic absorption spectrum.
authors.affiliation: Department of Chemistry, Imperial College of Science, Technology and Medicine, South Kensington, London, U.K.
authors.forename: A G
authors.initials: AG
authors.lastname: Montalban
authors.forename: W
authors.initials: W
authors.lastname: Jarrell
authors.forename: E
authors.initials: E
authors.lastname: Riguet
authors.forename: Q J
authors.initials: QJ
authors.lastname: McCubbin
authors.forename: M E
authors.initials: ME
authors.lastname: Anderson
authors.forename: A J
authors.initials: AJ
authors.lastname: White
authors.forename: D J
authors.initials: DJ
authors.lastname: Williams
authors.forename: A G
authors.initials: AG
authors.lastname: Barrett
authors.forename: B M
authors.initials: BM
authors.lastname: Hoffman
mesh_terms: D018360:Crystallography, X-Ray; D004563:Electrochemistry; D009682:Magnetic Resonance Spectroscopy; D008665:Metalloporphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet
chemical_list: D008665:Metalloporphyrins