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The interactions between cyclopentanocucurbit[6]uril (abbreviated as CyP6Q[6]) and a series of dialkyl-4,4′-bipyridinium and diaryl-4,4′-bipyridinium dicationic guest molecules, where the alkyl group is CH3(CH2) n with n = 0–6 (expressed as G1 to G7) and the aryl group is phenylene (G8) and xylene (G9), have been investigated in aqueous solution using 1H NMR spectroscopy, isothermal titration calorimetry (ITC), and electronic absorption spectroscopy. Our results show that G1 and G2 form 1 : 1 host–guest inclusion complexes with CyP6Q[6], in which the bipyridinium core is partially embedded in the cavity of CyP6Q[6]. G3 – G9 form 2 : 1 dumbbell-type host–guest inclusion complexes, in which the substituents are encapsulated by CyP6Q[6]. At the same time, CyP6Q[6] was compared with several other cucurbit[n]urils (Q[n]s) and their derivatives, such as Q[6], Q[7], and TMeQ[6], which have been reported to interact with this type of guest molecule. In its binding mode, CyP6Q[6] shows many interesting and different properties, and this difference was mainly reflected with G1 and G2. Although the host–guest chemistry of cucurbit[ n ]urils continues to flourish, that of the related cyclopentanocucurbit[6]uril (CyP6Q[6]) is at an embryonic stage. We are interested in the ability of CyP6Q[6] to include viologens, CyP6Q[6] shows many interesting and different properties, compared with other cucurbit[n]urils (Q[n]s) and their derivatives. [ABSTRACT FROM AUTHOR]