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Keywords:

  • Macrocyclic ligands;
  • Phthalocyanines;
  • Template synthesis;
  • Conformation analysis;
  • Copper

Abstract

A new zinc phthalocyaninate, bearing four flexible phenanthroline-containing 30-membered rings was synthesized by template condensation of a macrocyclic phthalonitrile. The resulting phthalocyanine was an insoluble aggregate. However, in the presence of CuI ions, the formation of a soluble complex was observed. UV/Vis and DOSY NMR spectroscopic studies showed a monomolecular state for this species in solution. 1H-1H ROESY demonstrated that the macrocyclic substituents adopt a folded conformation, giving the complex a globular shape. The folding originates from stacking interactions between the phthalocyanine core and peripheral copper(I)–phenanthroline complexes.