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

  • Suhang He
  • Chan Zhou
  • Haibo Zhang
  • Xiaohai Zhou
Original Article

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].

Keywords

Host–guest system Cucurbit[n]uril Binding behavior Supramolecular chemistry Pseudorotaxane 

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

Notes

Acknowledgments

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

Supplementary material

10847_2012_204_MOESM1_ESM.doc (2.2 mb)
Supplementary material 1 (DOC 2261 kb)

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Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  1. 1.College of Chemistry and Molecular SciencesWuhan UniversityWuhanPeople’s Republic of China

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