Rotaxane formation under thermodynamic control

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

*Corresponding author for this work

Research output: Contribution to journalArticle

94 Scopus citations

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 (US)
Pages (from-to)1363-1366
Number of pages4
JournalOrganic Letters
Volume1
Issue number9
DOIs
StatePublished - Nov 4 1999

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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