Chemistry of Heterocyclic Compounds

, Volume 49, Issue 12, pp 1740–1747 | Cite as

Synthesis, Spectral-Luminescent Properties, and Photostability of Zn(II) Complexes With Dipyrrins Modified by the Periphery and meso-Spacer

  • N. A. DudinaEmail author
  • A. Yu. Nikonova
  • Ye. V. Antina
  • M. B. Berezin
  • A. I. Vyugin

A comparative spectral-luminescent characterization was performed for the homoleptic zinc(II) chelates with dipyrrins containing four methyl or aryl substituents in the pyrrole rings and methine group or nitrogen atom as meso-spacer. It was shown that zinc dipyrrinates with substituted pyrrole rings and a methene spacer exhibited an intense fluorescence in nonpolar media. The phenyl-substituted complex had an order of magnitude stronger fluorescence than the methyl-substituted analog. Changing from a methene spacer to a nitrogen atom caused a substantial (up to 64 nm) red shift of the electronic absorption spectrum, and the chelate completely lost its fluorescent properties. The effects of the chelate ligand structure on the photostability of zinc(II) complexes were established.


azadipyrrin complex dipyrrin zinc photostability spectral-luminescent properties 


The authors are grateful to Professor, Dr. A. S. Semeikin (Ivanovo State University of Chemistry and Technology) for the contribution of ligands: 2-[(3,5-diphenyl-2Н-pyrrol-2-ylidene)methyl]-3,5-diphenyl-1Н-pyrrole and N-(3,5-diphenyl-2Н-pyrrol-2-ylidene)-3,5-diphenyl-1Н-pyrrol-2-amine, the synthesis of which will be published separately.


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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • N. A. Dudina
    • 1
    Email author
  • A. Yu. Nikonova
    • 2
  • Ye. V. Antina
    • 1
  • M. B. Berezin
    • 1
  • A. I. Vyugin
    • 1
  1. 1.G.A. Krestov Institute of Solution Chemistry, the Russian Academy of SciencesIvanovoRussia
  2. 2.Ivanovo State University of Chemistry and TechnologyIvanovoRussia

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