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New results are presented on the multicomponent supramolecular synthesis of pseudo[1]rotaxanes, achieved by designing pairs of structurally matching N-monoalkyl-4,4'-bipyridinium/2,7-diazapyrenium-based ligands having complementary π-donor/acceptor features, and intended to self-assemble into the targeted supramolecules by following integrative self-sorting processes. In all the studied cases, it was found that the envisioned species, characterized by NMR spectroscopy and MS spectrometry, arise as the main products of the self-assembly in