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Ion-pair electrostatic attraction-enhanced donor–acceptor interactions between the prototypic 1,4-dialkoxybenzene-viologen binding mode in water

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Abstract

Three electron-rich donor molecules D1–D3, which consist of one, two or four 1,4-bis(carboxylatomethoxy)benzene units, respectively, have been prepared. Donor–acceptor interactions between the di-, tetra- and octaanionic donors and electron-deficient bipyridinium derivatives A1–A3, which bear two methyl, benzyl, or 4-formylphenyl subunits, respectively, have been investigated using X-ray diffraction analysis (for the complex of D2 and A1) and 1H NMR and absorption experiments. It was revealed that D1 and D2 formed 1 : 1 donor–acceptor complexes with the three acceptors, while D3 formed 1 : 2 complexes with them. All the complexes exhibited high water-solubility. The crystal structure of complex D1·A1 showed that the biphenyl unit of D1 and the bipyridinium unit of A1 stacked alternately in the new perfect face-to-face pattern. By using isothermal titration calorimetric titration experiments, association constants for the 1 : 1 and 1 : 2 complexes in water were determined to be as high as 1.3 × 104 M−1 and 2.6 × 1011 M−2, respectively. The results supported that the intermolecular ion-pair electrostatic attraction between the carboxylate anions and the bipyridinium dication remarkably enhanced the intermolecular donor–acceptor interaction in water.

Graphical abstract: Ion-pair electrostatic attraction-enhanced donor–acceptor interactions between the prototypic 1,4-dialkoxybenzene-viologen binding mode in water

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Publication details

The article was received on 17 Dec 2017, accepted on 05 Jan 2018 and first published on 08 Jan 2018


Article type: Research Article
DOI: 10.1039/C7QO01126A
Citation: Org. Chem. Front., 2018, Advance Article
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    Ion-pair electrostatic attraction-enhanced donor–acceptor interactions between the prototypic 1,4-dialkoxybenzene-viologen binding mode in water

    Y. Zhang, S. Yu, B. Yang, H. Wang, D. Zhang and Z. Li, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO01126A

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