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.