Rectangular-shaped expanded phthalocyanines with two central metal atoms

J Am Chem Soc. 2012 Feb 22;134(7):3411-8. doi: 10.1021/ja209589x. Epub 2012 Feb 8.

Abstract

Expanded phthalocyanine (Pc) congeners with two Mo or W central metal ions and four isoindole ring moieties have been synthesized using normal Pc formation conditions in the presence of urea. The products have been characterized by electrochemistry; mass spectrometry (MS); IR, electron paramagnetic resonance (EPR), NMR, electronic absorption, and magnetic circular dichroism (MCD) spectroscopies; and X-ray analysis. The X-ray structures have rectangular C(2v) symmetry and provide evidence that the central Mo atoms are linked by a single bond and coordinated by two isoindole nitrogen atoms and two nitrogen atoms from the amine moieties. The electronic absorption bands extend into the 1200-1500 nm region. This can be explained using Gouterman's four-orbital theory. The experimental NMR data and theoretical calculations provide evidence for a heteroaromatic 22-π-electron conjugation system for the ring-expanded Pc system, which satisfies Hückel's (4n + 2)π aromaticity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Electron Spin Resonance Spectroscopy
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Isoindoles / chemical synthesis
  • Isoindoles / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Models, Molecular
  • Molybdenum / chemistry*
  • Tungsten / chemistry*

Substances

  • Indoles
  • Isoindoles
  • Molybdenum
  • phthalocyanine
  • Tungsten