Ammonium ion binding with pyridine-containing crown ethers

Theresa Chang, Aaron M. Heiss, Stuart J. Cantrill, Matthew C T Fyfe, Anthony R. Pease, Stuart J. Rowan, J. Fraser Stoddart, Andrew J P White, David J. Williams

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Dipyrido[24]crown-8 (DP24C8) has been synthesized and shown to form [2]pseudorotaxanes spontaneously with dibenzylammonium ions. These complexes, which have been demonstrated by 1H NMR spectroscopy to form faster in solution than when the macrocyclic polyether is dibenzo[24]crown-8 (DB24C8), are also stronger than their DB24C8 counterparts. One of the [2]pseudorotaxanes has been used to construct a [2]rotaxane (see above) comprising a dumbbell-shaped component based on a dibenzylammonium ion which is encircled by a DP24C8 macrocycle and terminated by (triphenylphosphonium)methyl stoppers.

Original languageEnglish
Pages (from-to)2947-2950
Number of pages4
JournalOrganic Letters
Issue number19
Publication statusPublished - 2000 Sep 21
Externally publishedYes

ASJC Scopus subject areas

  • Molecular Medicine

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    Chang, T., Heiss, A. M., Cantrill, S. J., Fyfe, M. C. T., Pease, A. R., Rowan, S. J., Stoddart, J. F., White, A. J. P., & Williams, D. J. (2000). Ammonium ion binding with pyridine-containing crown ethers. Organic Letters, 2(19), 2947-2950.