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Iodide Discrimination by Tetra‐Iodotriazole Halogen Bonding Interlocked Hosts
Author(s) -
Klein Harry A.,
Beer Paul D.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201806093
Subject(s) - rotaxane , iodide , chemistry , halogen bond , cationic polymerization , halogen , hydrogen bond , halide , catenane , host–guest chemistry , selectivity , pyridinium , supramolecular chemistry , polymer chemistry , photochemistry , molecule , inorganic chemistry , organic chemistry , alkyl , catalysis
Whilst the exploitation of interlocked host frameworks for anion recognition is widely established, examples incorporating halogen bond donor groups are still relatively rare. Through the integration of a novel tetra(iodotriazole)‐pyridinium motif into macrocycle and axle components, a family of halogen bonding catenane and rotaxanes are constructed for anion recognition studies in a competitive aqueous‐organic solvent mixture. Importantly, the degree of anion selectivity displayed is dictated by the topological nature and charged state of the respective interlocked host cavity. All the interlocked hosts exhibit iodide anion selectivity over other halides and sulfate, with the level of discrimination being the greatest with the mono‐cationic rotaxane. Arising from greater electrostatic interactions working in tandem with halogen bonding and hydrogen bonding, the di‐cationic rotaxane displays stronger anion association at the expense of a relatively lower degree of iodide selectivity.