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This chapter describes the recent progress in cucurbit[6]uril (CB[6])-based polymeric materials with an emphasis on polymer nanocapsules and two-dimensional (2D) polymer films. The development of the direct functionalization of CB[6] allowed chemists to synthesize CB[6] derivatives with multiple reactive functional groups at the periphery that can be polymerized to produce highly cross-linked two-dimensional polymer networks, which can eventually turn into polymer nanocapsules or two-dimensional polymer films having accessible CB[6] cavities. Unique structural features of the functionalized CB[6]s including a rigid, disc-shaped core and multiple polymerizable functional groups at the periphery allow the production of such covalently self-assembled nanostructured materials without the aid of templates or preorganization of monomers. Covalent and non-covalent post-synthetic modification can easily alter the surface properties of the polymer nanocapsules and 2D polymer films, which make them useful in a wide range of applications including drug delivery, biomedical imaging, catalysis, and separation. Furthermore, the two different morphologies (nanocapsule and 2D film) can be reversibly interconverted by solvent variation when the reversible disulfide linkages are exploited to cross-link the functionalized CB[6].

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