Single-Atom Tuning of Pyridine-Strapped Pillar[5]arene Capsules for Specific Guest Binding

Ruengsuk A.Vigromsitdet S.Saekee A.Wichannananon P.Sangtawesin T.Sukwattanasinitt M.Tantirungrotechai J.Harding D.J.Bunchuay T.Mahidol University2025-03-082025-03-082025-01-01Organic Letters (2025)15237060https://repository.li.mahidol.ac.th/handle/123456789/105550Pyridine bis(carboxamide)-strapped pillar[5]arene capsules were synthesized with the serendipitous formation of macrotricyclic products. The structural integrity of the supramolecular capsules, determined by the specific orientation of a single nitrogen atom, controls the electronic properties of the confined binding cavity, facilitating length-selective recognition of aliphatic organic guests with nitrile, isocyanide, and amine functional groups with exceptional host-guest binding affinity and selectivity for 1,2-diaminoethane (Ka > 104 M-1) in a polar organic solvent.ChemistryBiochemistry, Genetics and Molecular BiologySingle-Atom Tuning of Pyridine-Strapped Pillar[5]arene Capsules for Specific Guest BindingArticleSCOPUS10.1021/acs.orglett.5c001102-s2.0-8521885348815237052