Rotaxane formation under thermodynamic control

Stuart J. Cantrill; Stuart J. Rowan; J. Fraser Stoddart

Rotaxane formation under thermodynamic control

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

107 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 language	English
Pages (from-to)	1363-1366
Number of pages	4
Journal	Organic Letters
Volume	1
Issue number	9
Publication status	Published - 1999 Nov 4
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine

Cite this

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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.",

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year = "1999",

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T1 - Rotaxane formation under thermodynamic control

AU - Cantrill, Stuart J.

AU - Rowan, Stuart J.

AU - Stoddart, J. Fraser

PY - 1999/11/4

Y1 - 1999/11/4

N2 - 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.

AB - 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.

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SN - 1523-7060

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JO - Organic Letters

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Rotaxane formation under thermodynamic control

Abstract

ASJC Scopus subject areas

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