Novel porphyrazines containing peripherally functionalized macrocyclic (N2O2, N2S2) units: Synthesis and characterization


DYES AND PIGMENTS, vol.80, no.1, pp.187-193, 2009 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 80 Issue: 1
  • Publication Date: 2009
  • Doi Number: 10.1016/j.dyepig.2008.07.002
  • Journal Name: DYES AND PIGMENTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.187-193
  • Karadeniz Technical University Affiliated: No


Novel maleonitrile moieties were synthesized by cyclization of 2,3-bis[(2-pyridylmethyl)amino]-2(Z)-butene-1,4-dinitrile with 1,2-bis(2-iodoethoxy)-4-nitrobenzene or o-xylyenebis(1-chloro-3-thiapropane) under conditions of high dilution. A series of novel, free-base, magnesium and zinc porphyrazines bearing macrocyclic substituents in peripheral positions were prepared via Linstead macrocyclization reactions of different maleonitrile derivatives, 12-nitro-4,7-bis(pyridin-2-ylmethyl)-2,3,4,7,8,9-hexahydro-1,10,4,7-benzodioxa-diaza-cyclododecine-5,6-dicarbonitrile or 5,8-bis(pyridin-2-ylmethyl)-1,3,4,5,8, 9,10,12-octa-hydro-2,11,5,8-benzodi-thiadiazacyclo-tetradecine-6,7-dicarbonitrile and the corresponding divalent metal salts. Pentanuclear copper(II) complexes were also prepared from the corresponding zinc(II) porphyrazine derivatives. The compounds were characterized by a combination of elemental analysis, FT-IR, UV-vis, H-1 NMR, C-13 NMR and MS spectral data. (c) 2008 Elsevier Ltd. All rights reserved.