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Host–guest complexes of some cucurbit[n]urils with the hydrochloride salts of some imidazole derivatives

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An Erratum to this article was published on 27 February 2009

Abstract

Interaction between the normal cucurbit[n]urils (n = 6,7,8; Q[6], Q[7], Q[8]) and a sym-tetramethyl-substituted cucurbit[6]uril derivative (TMeQ[6]) with the hydrochloride salts of some imidazole derivatives N-(4-hydroxylphenyl)imidazole (g1), N-(4-aminophenyl)imidazole (g2), 2-phenylimidazole (g3) in aqueous solution was investigated by using 1H NMR spectroscopy, electronic absorption spectroscopy and fluorescence spectroscopy, as well as by using a single crystal X-ray diffraction determination. The 1H NMR spectra analysis established a basic interaction model in which inclusion complexes with a host:guest ratio of 1:1 forms for the Q[6]s and Q[7] cases, while with a host:guest ratio of 1:2 form for the Q[8] cases. It was common that the hosts selectively bound the phenyl moiety of the guests. Absorption spectrophotometric and fluorescence spectroscopic analysis in aqueous solution defined the stability of the host–guest inclusion complexes at pH 5.8 with a host:guest ratio of 1:1 form quantitatively as logK values between 4 and 5 for the smaller hosts Q[6 or 7]s, while with a host:guest ratio of 1:2 form quantitatively as logK values between 11 and 12 for the host Q[8]. Two single crystal X-ray structures of the inclusion complexes TMeQ[6]-g2 · HCl and TMeQ[6]-g3 · HCl showed the phenyl moiety of these two guests inserted into the host cavity, which supported particularly the 1H NMR spectroscopic study in solution.

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Acknowledgements

Support of the National Natural Science Foundation of China (NSFC; No. 20662003 and 20767001), the “Chun-Hui” Funds of Chinese Ministry of Education, the Science and Technology Fund of Guizhou Province and the International Collaborative Project Fund of Guizhou province are gratefully acknowledged.

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  1. Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, 550025, People’s Republic of China

    Yan Feng, Sai-Feng Xue, Zhi-Fang Fan, Yun-Qian Zhang, Qian-Jiang Zhu & Zhu Tao

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  1. Yan Feng
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Correspondence to Sai-Feng Xue.

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An erratum to this article can be found at http://dx.doi.org/10.1007/s10847-009-9553-6

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Feng, Y., Xue, SF., Fan, ZF. et al. Host–guest complexes of some cucurbit[n]urils with the hydrochloride salts of some imidazole derivatives. J Incl Phenom Macrocycl Chem 64, 121–131 (2009). https://doi.org/10.1007/s10847-009-9544-7

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