Issue 14, 2007

Chemically controlled self-assembly of [2]pseudorotaxanes based on 1,2-bis(benzimidazolium)ethane cations and 24-crown-8 macrocycles

Abstract

Cations derived from 1,2-bis(benzimidazolium)ethane can penetrate the cavity of dibenzo-24-crown-8 macrocycles to produce a new family of [2]pseudorotaxanes. These supramolecular structures are held together by a series of charge-assisted hydrogen bonds (+)N–H⋯O, ion-dipole and π-stacking interactions. These new adducts were fully characterised by NMR spectroscopy, ESI mass spectrometry and single-crystal X-ray diffraction. The effect of electron-donating and electron-withdrawing groups on the association constants was also analyzed. Chemical control of the threading/unthreading process was acheived by the alternate addition of acid and base.

Graphical abstract: Chemically controlled self-assembly of [2]pseudorotaxanes based on 1,2-bis(benzimidazolium)ethane cations and 24-crown-8 macrocycles

Supplementary files

Article information

Article type
Paper
Submitted
14 May 2007
Accepted
29 May 2007
First published
20 Jun 2007

Org. Biomol. Chem., 2007,5, 2252-2256

Chemically controlled self-assembly of [2]pseudorotaxanes based on 1,2-bis(benzimidazolium)ethane cations and 24-crown-8 macrocycles

D. Castillo, P. Astudillo, J. Mares, F. J. González, A. Vela and J. Tiburcio, Org. Biomol. Chem., 2007, 5, 2252 DOI: 10.1039/B707211B

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