title: Anion receptors based on halogen bonding with halo-1,2,3-triazoliums.
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.
authors: †Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany.|‡Jena Center for Soft Matters (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, 07743 Jena, Germany.
authors: Ronny
authors: R
authors: Tepper
authors: †Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany.|‡Jena Center for Soft Matters (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, 07743 Jena, Germany.
authors: Benjamin
authors: B
authors: Schulze
authors: †Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany.|‡Jena Center for Soft Matters (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, 07743 Jena, Germany.
authors: Michael
authors: M
authors: Jäger
authors: †Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany.|‡Jena Center for Soft Matters (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, 07743 Jena, Germany.
authors: Christian
authors: C
authors: Friebe
authors: §Leibniz Institute for Natural Product Research and Infection Biology - Hans Knöll Institute, Beutenbergstr. 11a, 07745 Jena, Germany.
authors: Daniel H
authors: DH
authors: Scharf
authors: ∥Laboratory of Inorganic and Analytical Chemistry, Friedrich Schiller University Jena, Lessingstr. 8, 07743 Jena, Germany.
authors: Helmar
authors: H
authors: Görls
authors: †Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstr. 10, 07743 Jena, Germany.|‡Jena Center for Soft Matters (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, 07743 Jena, Germany.
authors: Ulrich S
authors: US
authors: Schubert
mesh_terms: D000838:Anions / Q000737:chemistry; D001665:Binding Sites; D006219:Halogens / Q000737:chemistry*; D015394:Molecular Structure; D011789:Quantum Theory; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000838:Anions; D006219:Halogens; D014230:Triazoles