Covalently linked 5,15-diazaporphyrin dimers: Promising scaffolds for a highly conjugated azaporphyrin π system

Yoshihiro Matano, Daisuke Fujii, Tarou Shibano, Ko Furukawa, Tomohiro Higashino, Haruyuki Nakano, Hiroshi Imahori

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

The first examples of β-β directly linked, acetylene-bridged, and butadiyne-bridged 5,15-diazaporphyrin dimers have been prepared by palladium-catalyzed coupling reactions of nickel(II) and copper(II) complexes of 3-bromo-10,20-dimesityl-5,15-diazaporphyrin (mesityl=2,4,6-trimethylphenyl). The effects of the linking modes and meso-nitrogen atoms on the structural, optical, electrochemical, and magnetic properties of the distributed π systems were investigated by using X-ray crystallography, UV/Vis absorption spectroscopy, DFT calculations, cyclic voltammetry, and ESR spectroscopy. Both the electronic and steric effects of the meso-nitrogen atoms play an important role in the highly coplanar geometry of the directly linked dimers. The direct β-β linkage produces enhanced π conjugation and electron-spin coupling between the two diazaporphyrin units.

Original languageEnglish
Pages (from-to)3342-3349
Number of pages8
JournalChemistry - A European Journal
Volume20
Issue number12
DOIs
Publication statusPublished - Mar 17 2014

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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