期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 18, 期 18, 页码 5589-5605出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201103434
关键词
click chemistry; cucurbituril; molecular threading; pseudorotaxanes; rotaxanes
资金
- Israel Science Foundation
- German-Israeli Project Cooperation (DIP)
- Institute of Catalysis Science and Technology, Technion
- Open University
- Skaggs Institute for Chemical Biology
Bistable rotaxanes are important design elements of molecular devices for a broad range of applications, such as controlled drug release, molecular rotary motors, and chemical sensors. The hostguest complexes of cucurbit[6]uril and 1,4-bis(alkylaminomethyl)benzene were found to exhibit two stable binding modes with an unexpectedly high barrier between them. Their structural and dynamic properties, kinetic and thermodynamic parameters, as well as different chemical reactivity towards the azidealkyne [3+2] cycloaddition reaction (click chemistry), were discovered by NMR spectroscopy, X-ray crystallography, and isothermal titration microcalorimetry. The highly stable 2:1 complex, which is formed at room temperature, was found to be a kinetic product, which may be converted to the thermodynamic 1:1 complex upon prolonged heating to 100 degrees C. The latter is a very stable rotaxane despite the fact that it lacks bulky end groups.
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