Rotaxane formation under thermodynamic control

Stuart J. Cantrill, Stuart J. Rowan, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

107 Citations (Scopus)


Thermodynamic control operates in the synthesis of a [2]rotaxane based upon the dibenzylammonium ion/crown ether recognition motif. When dibenzo[24]crown-8 is added to an acetonitrile solution containing a diimine dumbbell-like component, the dynamic nature of the system (i.e., imine hydrolysis/reformation) offers the ring component access to the NH2+ center, allowing the self-assembly of the corresponding "dynamic" [2]rotaxane to occur. The "fixing" of this [2]rotaxane can be achieved upon reduction of the imine bonds, affording a kinetically inert [2]rotaxane.

Original languageEnglish
Pages (from-to)1363-1366
Number of pages4
JournalOrganic Letters
Issue number9
Publication statusPublished - 1999 Nov 4
Externally publishedYes

ASJC Scopus subject areas

  • Molecular Medicine


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