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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Acid/Base-mediated uptake and release of halide anions with a preorganized aryl-triazole foldamer
Wei Zhao1, Ying Wang, Jie Shang
1CAS 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).
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.
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