Multitopic dibenzylammonium, derivatives (4) of C-60 were prepared by Bingel reactions of C-60 with a malonate diester (2) containing two t-BOC protected dibenzylamine moieties, followed by deprotection and protonation. Self-assembly of model pseudorotaxanes 5 from the multidibenzylammonium C-60 derivatives with dibenzo-24-crown-8 was studied by H-1 NMR spectroscopy and mass spectrometry. Self-assembly of linear and star-shaped pseudorotaxanes 8 with up to 12 arms based on polystyrenes bearing terminal DB24C8 host units (7) and the guest functionalized C-60 salts was demonstrated by H-1 NMR spectroscopy and solution phase viscometry. These studies provide further evidence of the potential of supramacromolecular chemistry in construction of complex polymeric architectures. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47:6472-6495, 2009