Rotaxane or pseudorotaxane? That is the question!

Peter R. Ashton, Ian Baxter, Matthew C T Fyfe, Francisco Raymo, Neil Spencer, J. Fraser Stoddart, Andrew J P White, David J. Williams

Research output: Contribution to journalArticle

248 Citations (Scopus)

Abstract

A series of secondary dialkylammonium ions (RCH2)2NH2+ have been prepared, and their binding properties toward the macrocyclic polyether dibenzo[24]crown-8 (DB24C8) evaluated. By using this information, a route to a kinetically stable rotaxane-like entity - stabilized by noncovalent bonding interactions between the DB24C8 macroring and the ammonium center - was established, in which the crown ether slips over a dialkylammonium ion's stopper groups (R). However, we have found that the kinetic stability of this rotaxane-like entity is extremely dependent on the nature of the solvent in which it is dissolved, suggesting that pseudorotaxanes lie in the fuzzy domain between two sets of extremes, wherein a beadlike macrocycle and a dumbbell-like component may either (1) exist as a rotaxane or (2) be completely disassociated from one another.

Original languageEnglish
Pages (from-to)2297-2307
Number of pages11
JournalJournal of the American Chemical Society
Volume120
Issue number10
DOIs
StatePublished - Mar 18 1998
Externally publishedYes

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Rotaxanes
Crown ethers
Polyethers
Ions
Crown Ethers
Kinetics
Ammonium Compounds

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Ashton, P. R., Baxter, I., Fyfe, M. C. T., Raymo, F., Spencer, N., Stoddart, J. F., ... Williams, D. J. (1998). Rotaxane or pseudorotaxane? That is the question! Journal of the American Chemical Society, 120(10), 2297-2307. https://doi.org/10.1021/ja9731276

Rotaxane or pseudorotaxane? That is the question! / Ashton, Peter R.; Baxter, Ian; Fyfe, Matthew C T; Raymo, Francisco; Spencer, Neil; Stoddart, J. Fraser; White, Andrew J P; Williams, David J.

In: Journal of the American Chemical Society, Vol. 120, No. 10, 18.03.1998, p. 2297-2307.

Research output: Contribution to journalArticle

Ashton, PR, Baxter, I, Fyfe, MCT, Raymo, F, Spencer, N, Stoddart, JF, White, AJP & Williams, DJ 1998, 'Rotaxane or pseudorotaxane? That is the question!', Journal of the American Chemical Society, vol. 120, no. 10, pp. 2297-2307. https://doi.org/10.1021/ja9731276
Ashton PR, Baxter I, Fyfe MCT, Raymo F, Spencer N, Stoddart JF et al. Rotaxane or pseudorotaxane? That is the question! Journal of the American Chemical Society. 1998 Mar 18;120(10):2297-2307. https://doi.org/10.1021/ja9731276
Ashton, Peter R. ; Baxter, Ian ; Fyfe, Matthew C T ; Raymo, Francisco ; Spencer, Neil ; Stoddart, J. Fraser ; White, Andrew J P ; Williams, David J. / Rotaxane or pseudorotaxane? That is the question!. In: Journal of the American Chemical Society. 1998 ; Vol. 120, No. 10. pp. 2297-2307.
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