Aggregation behaviors of phthalocyanine derivatives which have a dendritic structure were examined in an aqueous solution. We prepared the first- and second-generation dendrimers (WG1-PC and WG2-PC), having water-soluble substituents as a peripheral group, to be resolved in water. From spectroscopic measurement, WG2-PC acted in a monomeric manner, even in an aqueous solution, in contrast to WG 1-PC, which exhibited spectra attributed to aggregation. This implies that a higher generation of water-soluble dendrimers can prevent a phthalocyanine core from forming an aggregation. The introduction of the second-generation dendrons to an aggregatable core may be effective to avoid self-aggregation and an undesirable deactivation process. Copyright (C) 2007 Society of Porphyrins & Phthalocyanines.