title: Acid/Base-mediated uptake and release of halide anions with a preorganized aryl-triazole foldamer.
abstract: A new approach for the construction of artificial receptors capable of selectively uptake and release of halides to mimic the biological halide ions pumps is developed, in which the preorganized aryl-triazole foldamer was designed to bear a resorcinolic group in the central strand as a switch regulator. By using 1,8-diazabicyclo[5.4.0]undec-7-ene/picric acid as the trigger, the foldamer can be switched between "w"-shape and helical conformation. Due to the large, half-open cavity as well as the additional electrostatic repulsion between oxyanions and guest halide, the foldamer in "w"-shape possesses a much weaker affinity for chloride, bromide, and iodide anions than those in the helical conformation in 6:94 (v/v) [D6 ]DMSO/CDCl3 . When the foldamer and chloride ions have the same initial concentrations of 1 mM, 70 % chloride ions in the solution could be reversibly bound or released upon switching.
authors.affiliation: CAS Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (P. R. China); University of Chinese Academy of Sciences, Beijing 100049 (P. R. China).
authors.forename: Wei
authors.initials: W
authors.lastname: Zhao
authors.forename: Ying
authors.initials: Y
authors.lastname: Wang
authors.forename: Jie
authors.initials: J
authors.lastname: Shang
authors.forename: Yanke
authors.initials: Y
authors.lastname: Che
authors.forename: Hua
authors.initials: H
authors.lastname: Jiang
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010851:Picrates / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D002712:Chlorides; D010851:Picrates; D014230:Triazoles; C005858:picric acid; C031033:1,8-diazabicyclo(5.4.0)undec-7-ene
keywords: acid/base-mediation; anion regulation; foldamers; resorcinolic groups; switches