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

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.

Citation

Xu, W., Kan, J., Yang, B., Prior, T. J., Bian, B., Xiao, X., Tao, Z., & 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

• Journal Article Type: Article
• Acceptance Date: Nov 20, 2018
• Online Publication Date: Nov 21, 2018
• Publication Date: Jan 4, 2019
• Deposit Date: Dec 3, 2018
• Publicly Available Date: Nov 22, 2019
• Journal: Chemistry - An Asian Journal
• Print ISSN: 1861-4728
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 14
• Issue: 1
• Pages: 235-242
• DOI: https://doi.org/10.1002/asia.201801498
• Keywords: General Chemistry
• Public URL: https://hull-repository.worktribe.com/output/1171140
• Publisher URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/asia.201801498
• Contract Date: Dec 3, 2018