Pseudo[2,3]rotaxanes have been successfully fabricated by the complexation of cucurbit[8]uril (CB[8]) macrocycles with extended viologen derivatives. Two design rules enable the incorporation of a third CB[8] onto a recently reported pseudo[2,2]rotaxane. Incorporation of a third macrocycle confines the dimeric stacking of chromophores into specific alignment, leading to effective electron-delocalisation along their long molecular axis.