Synthesis and characterization of periphery-functionalized porphyrazines containing mixed pyrrolyl and pyridylmethylamino groups

Tomasz Goslinski*, Ewa Tykarska, Wojciech Szczolko, Tomasz Osmalek, Aleksandra Smigielska, Stanislaw Walorczyk, Hong Zong, Maria Gdaniec, Brian M. Hoffman, Jadwiga Mielcarek, Stanislaw Sobiak

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

The condensation reaction of 2-amino-3-[(3-pyridylmethyl)amino]-2(Z)- butene-1,4-dinitrile with a series of diketones led to novel dinitriles, of which 2-(2,5-dimethyl-1H-pyrrol-1-yl)-3-[methyl(3-pyridylmethylene)amino]-2(Z)- butene-1,4-dinitrile, the product of the Paal-Knorr reaction, was successfully utilized in the Linstead macrocyclization towards symmetrical and unsymmetrical porphyrazines. NMR and X-ray study revealed an almost perpendicular orientation of the pyrrolyl groups in relation to the porphyrazine platform. The newly synthesized macrocycles with different peripheral groups show interesting spectroscopic and electrochemical properties. Due to selective sensor/coordination properties they are expected to find applications as chemical sensors and electronic materials.

Original languageEnglish (US)
Pages (from-to)223-234
Number of pages12
JournalJournal of Porphyrins and Phthalocyanines
Volume13
Issue number2
DOIs
StatePublished - Feb 2009

Keywords

  • Cyclic voltammetry
  • Diketones
  • Linstead macrocyclization
  • Porphyrazine
  • Spectroscopy

ASJC Scopus subject areas

  • Chemistry(all)

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