Rotaxane or Pseudorotaxane? That Is the Question!

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 interacti...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1998-03, Vol.120 (10), p.2297-2307
Main Authors: Ashton, Peter R, Baxter, Ian, Fyfe, Matthew C. T, Raymo, Françisco M, Spencer, Neil, Stoddart, J. Fraser, White, Andrew J. P, Williams, David J
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja9731276