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Host-guest complexes of a water soluble cucurbit[6]uril derivative with some dications of 1,ω-alkyldipyridines: 1H NMR and X-ray structures

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Abstract

Interactions between a symmetrical tetramethyl-substituted cucurbit[6]uril (host: TMeQ[6]) and 1,ω-alkylenedipyridine (ω = 2, 4, 6, 8, 10) dicationic guests were investigated using 1H NMR spectroscopy and single crystal X-ray crystallography. In these inclusion complexes, combined cavity and portal binding in TMeQ[6] were observed, and the length of the bridged alkylene was found to play an important role not only in balancing the overall hydrophilic/hydrophobic interaction between the host and the guest, but also in defining the structure of the resulting inclusion complexes. For the guest 1,2-ethylenedipyridine (Edpy), TMeQ[6] includes a positively charged pyridine ring of Edpy to form an unsymmetrical inclusion complex; for the guest 1,4-butylenedipyridine (Bdpy), TMeQ[6] includes a positively charged pyridine ring of Bdpy, but the different competitive interactions in and between the related inclusion complexes could lead to a fast exchange between the hosts and guests. For the guests with longer bridge chains, such as 1,6-hexamethylenedipyridine (Hdpy) or 1,8-octylenedipyridine (Odpy), a stable pseudorotaxane inclusion complex is formed by combining the hydrophobic cavity and the outer portal dipole-ion interactions. However, for 1,10-decatylenedipyridine (Ddpy), the two TMeQ[6] host molecules include the two end pyridine rings of Ddpy and form a dumbbell inclusion complex.

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Authors and Affiliations

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

    Xin Xiao, YunQian Zhang, QianJiang Zhu, SaiFeng Xue & Zhu Tao

  2. Institute of Applied Chemistry, Guizhou University, Guiyang, 550025, China

    Xin Xiao, QianJiang Zhu, SaiFeng Xue & Zhu Tao

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  1. Xin Xiao
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  2. YunQian Zhang
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  3. QianJiang Zhu
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  4. SaiFeng Xue
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  5. Zhu Tao
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Correspondence to Zhu Tao.

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Supported by the National Natural Science Foundation of China (Grant Nos. 20662003 & 20767001), the International Collaborative Project of Guizhou Province (Grant No. 2007400108), the Science Technology Fund of Guizhou Province (Grant No. J-2008-2012) and the Natural Science Youth Foundation of Guizhou University (Grant No. 2007-005)

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Xiao, X., Zhang, Y., Zhu, Q. et al. Host-guest complexes of a water soluble cucurbit[6]uril derivative with some dications of 1,ω-alkyldipyridines: 1H NMR and X-ray structures. Sci. China Ser. B-Chem. 52, 475–482 (2009). https://doi.org/10.1007/s11426-009-0089-9

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  • DOI: https://doi.org/10.1007/s11426-009-0089-9

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