Alkyl substituted 4-pyrrolidinopyridinium salts encapsulated in the cavity of cucurbit[10]uril

Xu, Weitao; Liu, Ming; Escaño, Mary Clare; Redshaw, Carl; Bian, Bing; Fan, Ying; Tao, Zhu; Xiao, Xin

Abstract

The interaction between cucuribit[10]uril (Q[10]) 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 and mass spectrometry. The results revealed that the guests g1–g5 are located completely inside the cavity differing only in the orientation of g1, g4 and g5 which are aligned with the portal, whilst g2 and g3 are perpendicular to it. For g6, the tetrahydropyrrole moiety remains outside of the portal. DFT calculations confirm the stability of the guests in the Q[10] and the possibility of their curved structure inside the Q[10].

Citation

Xu, W., Liu, M., Escaño, M. C., Redshaw, C., Bian, B., Fan, Y., …Xiao, X. (in press). Alkyl substituted 4-pyrrolidinopyridinium salts encapsulated in the cavity of cucurbit[10]uril. New journal of chemistry = Nouveau journal de chimie, 43(18), 7028-7034. https://doi.org/10.1039/c9nj01089k

• Journal Article Type: Article
• Acceptance Date: Apr 8, 2019
• Online Publication Date: Apr 10, 2019
• Deposit Date: Apr 22, 2019
• Publicly Available Date: Apr 11, 2020
• Journal: New Journal of Chemistry
• Print ISSN: 1144-0546
• Electronic ISSN: 1369-9261
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 43
• Issue: 18
• Pages: 7028-7034
• DOI: https://doi.org/10.1039/c9nj01089k
• Keywords: Materials Chemistry; General Chemistry; Catalysis
• Public URL: https://hull-repository.worktribe.com/output/1634055
• Publisher URL: https://pubs.rsc.org/en/Content/ArticleLanding/2019/NJ/C9NJ01089K#!divAbstract
• Additional Information: This is the accepted manuscript of an article published in New journal of chemistry, 2019. The version of record is available at the DOI link in this record.