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Issue 44, 2018
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Enhancement of anion recognition exhibited by a zinc-imidazole-based ion-pair receptor composed of C–H hydrogen- and halogen-bond donor groups

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Abstract

A 2-haloimidazole-tetraphenylethylene ion-pair receptor 1 is shown to recognise only HSO4 anions in the presence of a cobound Zn2+ cation guest species, which induced a remarkable increase with concomitant blue shift of the emission band of the complex [1·2Zn]4+ whereas no affinity of the free receptor 1 by the anions is observed. In addition, the downfield shifts observed by 1H NMR of the Ha, Hb and Hc protons of the complex [1·2Zn]4+ upon the addition of HSO4 anions indicate their participation in the recognition event. According to DFT studies, upon chelating a Zn2+ cation with two imidazole nitrogen atoms, receptor 1 adopts a conformation ideally fitted to recognise HSO4 through a combination of C(sp2)–H⋯O and C(sp3)–H⋯O hydrogen bondings, C+(sp2)–Br⋯O halogen bonding and C(sp2)⋯O tetrel bonding.

Graphical abstract: Enhancement of anion recognition exhibited by a zinc-imidazole-based ion-pair receptor composed of C–H hydrogen- and halogen-bond donor groups

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Publication details

The article was received on 15 Sep 2018, accepted on 18 Oct 2018 and first published on 19 Oct 2018


Article type: Paper
DOI: 10.1039/C8DT03736A
Citation: Dalton Trans., 2018,47, 15941-15947
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    Enhancement of anion recognition exhibited by a zinc-imidazole-based ion-pair receptor composed of C–H hydrogen- and halogen-bond donor groups

    P. Sabater, F. Zapata, B. López, I. Fernández, A. Caballero and P. Molina, Dalton Trans., 2018, 47, 15941
    DOI: 10.1039/C8DT03736A

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