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Updated: Jul 2, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Indolocarbazole-based foldamers capable of binding halides in water
1Center for Bioactive Molecular Hybrids, Department of Chemistry, Yonsei University, Seoul, 120-749, S. Korea.
Abstract:
A series of indolocarbazole-based foldamers have been prepared which can fold into a helical array with an internal cavity encircled by multiple indole NHs, thus allowing for binding anions by hydrogen bonds. The helical folding has been confirmed by computer modeling, 1H NMR spectroscopy, 2D ROESY experiments, and binding studies. A water-soluble derivative binds small, hydrophilic anions in the order Cl- > F- > Br- but negligibly with large, diffuse anions such as I- and ClO4-. Interestingly, the relative binding affinities of the fluoride and chloride ions in water are opposite to each other in an organic medium 4:1 (v/v) DMSO/MeOH, possibly due to the difference in the competing solvation energy.
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