Synthesis of a new functionalized pillar[4]­arene[1]­quinone and its host–guest complexation with a bis-imidazolium dication was demonstrated. 1D/2D NMR spectroscopic analyses and high-resolution mass spectrometric analyses showed the formation of the pseudo[3]­rotaxane assembly upon host–guest complexation. 1H NMR titration experiments revealed the role of hydrogen bonding motifs in bringing positive cooperativity by comparing the binding constants for the host–guest complexation of pillar[4]­arene[1]­quinone with a bis-imidazolium guest. Anion-responsiveness of the pseudo[3]­rotaxane assembly was also demonstrated.

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