ArticleJournal of the American Chemical Society2026
Beyond Passive Substituents: Tosyl-Directed Self-Templation Enables Selective Pillar[4 + 1]arene Formation and Topology Switching.
Article in Journal of the American Chemical Society, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Substituents in supramolecular chemistry are usually treated as passive handles that tune solubility or reactivity rather than as active determinants of assembly pathways. Here we show that tosyl groups promote directional noncovalent recognition and thereby control both cocyclization selectivity and postassembly topology in pillararenes. Under otherwise identical conditions, brominated analogues give statistical mixtures in which the pillar[4 + 1]arene product appears at only 1-19% distribution, whereas tosyl-substituted monomers undergo pseudorotaxane-like preassembly that enables highly selective self-templated pillar[4 + 1]arene formation without added external templates. A crystallographic survey of 12 single-crystal structures (
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