Issue 31, 2019

Exploiting 1,4-naphthoquinone and 3-iodo-1,4-naphthoquinone motifs as anion binding sites by hydrogen or halogen-bonding interactions

Abstract

We describe here the utilization of 1,4-naphthoquinone and 3-iodo-1,4-naphthoquinone motifs as new anion binding sites by hydrogen- or halogen-bonding interactions, respectively. These binding sites have been integrated in bidentate ester based receptors. Emission experiments reveal that both receptors selectively recognize sulfate anions, which induced a remarkable increase of a new emission band attributed to the formation of π-stacking interactions between two 1,4-naphthoquinone units. Absorption spectroscopy and mass spectrometry indicate the disruption of the ester group of the 1,4-naphthoquinone based receptor in the presence of HP2O73−, H2PO4, F, AcO and C6H5CO2 and in the halogenated receptor with HP2O73−, F and AcO anions, while the presence of sulfate anions showed the clasical complexation behaviour. The 1H-NMR experiment showed a slow exchange process of the receptors with their sulfate complexes. The binding mode of the receptors with sulfate has been studied by DFT calculations along with the Molecular Electrostatic Potential (MEP) surface computational tool that reveals those parts of the receptors which are more suitable for interacting with anions.

Graphical abstract: Exploiting 1,4-naphthoquinone and 3-iodo-1,4-naphthoquinone motifs as anion binding sites by hydrogen or halogen-bonding interactions

Supplementary files

Article information

Article type
Paper
Submitted
14 May 2019
Accepted
02 Jul 2019
First published
02 Jul 2019

Dalton Trans., 2019,48, 11813-11821

Exploiting 1,4-naphthoquinone and 3-iodo-1,4-naphthoquinone motifs as anion binding sites by hydrogen or halogen-bonding interactions

E. Navarro-García, M. D. Velasco, F. Zapata, A. Bauzá, A. Frontera, C. Ramírez de Arellano and A. Caballero, Dalton Trans., 2019, 48, 11813 DOI: 10.1039/C9DT02012H

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