Issue 8, 2016

Recognition of silver cations by a cucurbit[8]uril-induced supramolecular crown ether

Abstract

The host–guest interaction of cucurbit[8]uril (Q[8]) with a synthesized guest molecule, consisting of naphthalene and viologen moieties bridged by a carbon oxygen chain, was investigated by 1H NMR and UV-Vis spectroscopy. The results indicated the formation of an inclusion complex in a ratio of 1 : 1 with a moderate association constant of Ka = (1.1 ± 0.2) × 106 L mol−1. The formation of this special complex is driven by the markedly enhanced charge-transfer interaction between the electron-rich and electron-deficient guest molecule inside the hydrophobic cavity of Q[8], while the carbon oxygen chain stays outside of Q[8] to form a supramolecular crown ether. Screening of the metal cation substrate suggested that the inclusion complex recognizes Ag+ ions with high selectivity, as shown by UV-Vis spectroscopy.

Graphical abstract: Recognition of silver cations by a cucurbit[8]uril-induced supramolecular crown ether

Supplementary files

Article information

Article type
Paper
Submitted
17 Dec 2015
Accepted
25 Jan 2016
First published
25 Jan 2016

Org. Biomol. Chem., 2016,14, 2556-2562

Recognition of silver cations by a cucurbit[8]uril-induced supramolecular crown ether

Q. Geng, F. Wang, H. Cong, Z. Tao and G. Wei, Org. Biomol. Chem., 2016, 14, 2556 DOI: 10.1039/C5OB02590G

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