Andrew DockerThanthapatra BunchuayMichael AhrensAntonio J. Martinez-MartinezPaul D. BeerUniversity of OxfordUniversidad de HuelvaMahidol University2022-08-042022-08-042021-05-20Chemistry - A European Journal. Vol.27, No.29 (2021), 7837-784115213765094765392-s2.0-85104996543https://repository.li.mahidol.ac.th/handle/20.500.14594/76529A series of chalcogen, halogen and hydrogen bonding heteroditopic macrobicyclic cryptands are reported and their potassium halide ion-pair recognition properties investigated. Saliently, the co-bound potassium cation was determined to be crucial in switching on the bromide and iodide recognition properties of the respective cryptand receptor. Importantly, the nature of the sigma-hole mediated interaction employed in the anion recognition component is demonstrated to significantly augment the ion-pair binding behaviour, markedly so for the halogen bonding analogue. Most notably the incorporation of a chelating chalcogen bonding donor motif significantly improves the selectivity towards KBr over KI, relative to halogen and hydrogen bonding analogues.Mahidol UniversityChemical EngineeringChemistryArticleSCOPUS10.1002/chem.202100579