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Updated: Apr 17, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Anion receptors based on halogen bonding with halo-1,2,3-triazoliums
Ronny Tepper1,2, Benjamin Schulze1,2, Michael Jäger1,2
1†Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany.
Abstract:
A systematic series of anion receptors based on bidentate halogen bonding by halo-triazoles and -triazoliums is presented. The influence of the halogen bond donor atom, the electron-withdrawing group, and the linker group that bridges the two donor moieties is investigated. Additionally, a comparison with hydrogen bond-based analogues is provided. A new, efficient synthetic approach to introduce different halogens into the heterocycles is established using silver(I)-triazolylidenes, which are converted to the corresponding halo-1,2,3-triazoliums with different halogens. Comprehensive nuclear magnetic resonance binding studies supported by isothermal titration calorimetry studies were performed with different halides and oxo-anions to evaluate the influence of key parameters of the halogen bond donor, namely, polarization of the halogen and the bond angle to the anion. The results show a larger anion affinity in the case of more charge-dense halides as well as a general preference of the receptors to bind oxo-anions, in particular sulfate, over halides.
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