Rotaxane formation under thermodynamic control

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

Research output: Contribution to journalArticle

93 Citations (Scopus)

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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Rotaxanes
Thermodynamics
imines
thermodynamics
Imines
fixing
acetonitrile
hydrolysis
self assembly
ethers
Crown Ethers
rings
synthesis
Self assembly
Hydrolysis
ions
Ions

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.

Rotaxane formation under thermodynamic control. / Cantrill, Stuart J.; Rowan, Stuart J.; Stoddart, J. Fraser.

In: Organic Letters, Vol. 1, No. 9, 04.11.1999, p. 1363-1366.

Research output: Contribution to journalArticle

Cantrill, SJ, Rowan, SJ & Stoddart, JF 1999, 'Rotaxane formation under thermodynamic control', Organic Letters, vol. 1, no. 9, pp. 1363-1366.
Cantrill SJ, Rowan SJ, Stoddart JF. Rotaxane formation under thermodynamic control. Organic Letters. 1999 Nov 4;1(9):1363-1366.
Cantrill, Stuart J. ; Rowan, Stuart J. ; Stoddart, J. Fraser. / Rotaxane formation under thermodynamic control. In: Organic Letters. 1999 ; Vol. 1, No. 9. pp. 1363-1366.
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