Synthesis and aggregation behaviour of phthalocyanines substituted with flexible crown ether

The synthesis of metal-free and metallo derivatives (Ni, Zn) of tetrasubstituted phthalocyanines (Pcs) obtained from 4-[methyleneoxy(d15-crown-5)]phthalonitrile is described. The new compounds have been characterized by elemental analyses, IR,H-1 and C-13 NMR, MS and UV-vis. The thermal stabilities of the compounds were determined by thermogravimetric analysis. The alkali metal ions bound to crown ether groups force dimerization of the phthalocyanine units in solution, as observed in the electronic spectra by the broadening of the Q band transition at 675 Nn. The highest affinity for potassium ion was observed in the case of the NiPc derivative in solvent extraction experiments. Copyright (C) 2000 John Wiley & Sons, Ltd.