A nanofiltration strategy for tailing pond waters (TPWs) that utilizes cyclodextrin (CD)-based polymeric materials as supramolecular sorbents is proposed. Naphthenic acids (NAs) from the Athabasca TPWs are investigated as the target sorbate molecules. The sorption properties of several supramolecular porous materials were characterized using equilibrium sorption isotherms in aqueous solution wherein electrospray ionization mass spectrometry was used to monitor the concentration of NAs in aqueous solution. The characterization of the supramolecular sorbents was performed using C-13 NMR and IR spectroscopy, while nitrogen porosimetry was used to estimate their surface area and pore structure properties. Independent estimates of surface area were obtained using a chromophore dye adsorption method in aqueous solution. The sorption results for NAs in solution were compared between a commercially available standard; granular activated carbon (GAC) and three types of synthetic materials. The sorption capacities for GAC ranged from 100 to 160 mg NAs/g of material whereas the polymeric materials ranged from 20 to 30 mg NAs/g of material over the experimental conditions investigated. In general, differences in the sorption properties between GAC and the CD-based sorbents were observed and related to differences in the surface areas of the materials and the chemical nature of the sorbents. The CD-based supramolecular materials displayed sorption capacities ranging from 36.2 to 657 m(2)/g as compared to that for GAC (795 m(2)/g). (C) 2008 Published by Elsevier B.V. on behalf of The Institution of Chemical Engineers.