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Binding modes of cucurbit[6]uril and cucurbit[7]uril with a series of bis-pyridinium compounds

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Abstract

Binding behaviors of cucurbit[6]uril (CB[6]) and cucurbit[7]uril (CB[7]) with a series of bis-pyridinium compounds N, N’-hexamethylenebis(1-alkyl-4-carbamoyl pyridinium bromide) (HBPB-n) (alkyl chain length, n = 6, 8 and 10) guests were investigated using 1H-NMR, ESI–MS and single crystal X-ray diffraction methods. The results show that CB[6] and CB[7] can form [2]pseudorotaxanes with HBPB-n easily. When increasing the length of tail alkyl chain, the binding site of CB[6] at guest molecules changed from the tail to the middle part, while CB[7] remained located over the tail chain. As CB[6] and CB[7] were added in HBPB-8 aqueous solution, a [3]pseudorotaxane was formed by the inclusion of the internal middle site in CB[6] and the tail chain in CB[7].

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Abbreviations

CB[n]:

Cucurbit[n]uril

HBPB-n:

N, N′-hexamethylenebis(1-alkyl-4-carbamoyl pyridinium bromide) (alkyl chain length, n)

4-BPH:

N, N′-bis(4-pyridinecarboxamide)-1,6-hexane

P8:

N-octylpyridinium bromide

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Acknowledgments

We are grateful to the National Natural Science Foundation of China (No. 20972120) for financial support.

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  1. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, Hubei, People’s Republic of China

    Suhang He, Chan Zhou, Haibo Zhang & Xiaohai Zhou

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  1. Suhang He
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Correspondence to Haibo Zhang or Xiaohai Zhou.

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He, S., Zhou, C., Zhang, H. et al. Binding modes of cucurbit[6]uril and cucurbit[7]uril with a series of bis-pyridinium compounds. J Incl Phenom Macrocycl Chem 76, 333–344 (2013). https://doi.org/10.1007/s10847-012-0204-y

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