Self-assembled molecular aggregates of fluoroalkyl end-capped N-(1,1-dimethyl-3-oxobutyl)- and N,N-dimethyl-acrylamide oligomers in methanol were found to interact with phthalocyanines as guest molecules to exhibit good solubility. On the other hand, the corresponding non-fluorinated oligomers were not effective in solubilizing phthalocyanines under similar conditions. In these oligomers, fluorinated N-(1,1-dimethyl-3-oxobutyl)acrylamide oligomers were more effective in solubilizing phthalocyanines in methanol. Self-assemblies formed by fluorinated oligomer-phthalocyanine complexes are applied to the surface modifications of polystyrene (PS), and the modified PS surface exhibited not only a strong oleophobicity imparted by fluorine but also good hydrophilicity. Thus, these fluorinated molecular aggregate-phthalocyanine systems are suggested to have high potential for new fluorinated functional materials through their excellent properties imparted by fluorine and phthalocyanines. (C) 2004 Wiley Periodicals, Inc.