Rotaxane Formation under Thermodynamic Control

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/refo...

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Bibliographic Details
Published inOrganic letters Vol. 1; no. 9; pp. 1363 - 1366
Main Authors Cantrill, Stuart J, Rowan, Stuart J, Stoddart, J. Fraser
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.11.1999
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SECONDARY DIALKYLAMMONIUM SALTS
CHEMISTRY
ROTAXANE
CATENANES
CROWN-ETHERS
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol990966j