Rotaxane formation under thermodynamic control

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

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Abstract

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
Volume1
Issue number9
Publication statusPublished - 1999 Nov 4
Externally publishedYes

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ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Cantrill, S. J., Rowan, S. J., & Stoddart, J. F. (1999). Rotaxane formation under thermodynamic control. Organic Letters, 1(9), 1363-1366.