In this article, we present the synthesis and characterization of water-soluble polymers with hydrophobic moieties. The polymers were synthesized in aqueous solutions utilizing beta-cyclodextrins as solubility enhancers to bring the hydrophobic monomers into solution. Polymers were made with different spacing between polymer backbone and phenyl moiety by using styrene, allylbenzene, and 4-phenyl-1-butene as hydrophobic moieties, respectively. The effect of the presence of CDs during synthesis as well as this difference in spacing was investigated by rebinding free beta-CDs to the polymers. The interactions between polymers and CDs were studied by ITC and this revealed some differences between the polymers. Polymers made in the presence of CDs showed a markedly stronger binding to free CDs. The same was observed with polymers with a longer spacing between backbone and phenyl moiety. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 6619-6629, 2009