Phthalocyanine-centred and naphthalocyanine-centred aryl ether dendrimers with oligo(ethyleneoxy) surface groups

The synthesis of the 1st, 2nd and 3rd generation phthalocyanine-centred and naphthalocyanine-centred poly(aryl ether) dendrimers possessing oligo(ethyleneoxy) surface groups is described. These materials are soluble in polar protic solvents. For both types of macrocycle, the tendency of the non-polar phthalocyanine core towards intermolecular cofacial aggregation is not reduced by peripheral dendritic substitution. However, the prohibition of cofacial aggregation can be achieved by placing the dendritic substituents at the axial sites of the silicon-containing macrocycle. A single crystal X-ray diffraction analysis of one of these compounds beautifully illustrates this concept.