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A study of the interaction between cucurbit[8]uril and alkyl substituted 4-pyrrolidinopyridinium salts

Xu, Weitao; Kan, Jinglan; Yang, Bo; Prior, Timothy J.; Bian, Bing; Xiao, Xin; Tao, Zhu; Redshaw, Carl

Authors

Weitao Xu

Jinglan Kan

Bo Yang

Bing Bian

Xin Xiao

Zhu Tao

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Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Abstract

The interaction between cucuribit[8]uril (Q[8]) and a series of 4-pyrrolidinopyridinium salts bearing aliphatic substituents at the pyridinium nitrogen, namely 4-(C4H8N)C5H5NRBr, where R = Et (g1), n-butyl (g2), n-pentyl (g3), n-hexyl (g4), n-octyl (g5), n-dodecyl (g6), has been studied in aqueous solution by 1H NMR spectroscopy, electronic absorption spectroscopy, Isothermal Titration Calorimetry and mass spectrometry. Single crystal X-ray diffraction revealed the structure of the host-guest complexes for g1, g2, g3, and g5. In each case the Q[8] contains two guest molecules in a centrosymmetric dimer. The orientation of the guest molecule changes as the alkyl chain increases in length. Interestingly, in the solid state, the inclusion complexes identified are different from those observed in solution, and furthermore, in the case of g3, Q[8] exhibits two different interactions with the guest. In solution, the length of the alkyl chain plays a significant role in determining the type of host-guest interaction present.

Journal Article Type Article
Publication Date Jan 4, 2019
Journal Chemistry - An Asian Journal
Print ISSN 1861-4728
Electronic ISSN 1861-471X
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 14
Issue 1
Pages 235-242
Institution Citation Xu, W., Kan, J., Yang, B., Prior, T. J., Bian, B., Xiao, X., …Redshaw, C. (2019). A study of the interaction between cucurbit[8]uril and alkyl substituted 4-pyrrolidinopyridinium salts. Chemistry - An Asian Journal, 14(1), 235-242. https://doi.org/10.1002/asia.201801498
DOI https://doi.org/10.1002/asia.201801498
Keywords General Chemistry
Publisher URL https://onlinelibrary.wiley.com/doi/abs/10.1002/asia.201801498