Efficient production of [n]rotaxanes by using template-directed clipping reactions
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香港中文大學研究人員
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摘要In this article, we report on the efficient synthesis of well defined, homogeneous [n]rotaxanes (n up to 11) by a template-directed thermodynamic clipping approach. By employing dynamic covalent chemistry in the form of reversible imine bond formation, [n]rotaxanes with dialkylammonium ion (-CH 2NH2+CH2-) recognition sites, encircled by [24]crown-8 rings, were prepared by a thermodynamically controlled, template-directed clipping procedure, that is, by mixing together a dumbbell compound containing a discrete number of -CH2NH2 +CH2- ion centers with appropriate amounts of a dialdehyde and a diamine to facilitate the [n]rotaxane formation. A 21-component self-assembly process is operative during the formation of the [11]rotaxane. The oligomeric dumbbells containing -CH2NH2 +CH2- ion recognition sites were prepared by a stepwise protocol. Several of the dynamic [n]rotaxanes were converted into their kinetically stable counterparts, first by reduction ("fixing") of imine bonds with the BH3·THF complex, then by protonation of the complex by addition of acid. © 2007 by The National Academy of Sciences of the USA.
著者Wu J., Leung K.C.-F., Stoddart J.F.
期刊名稱Proceedings of the National Academy of Sciences
出版年份2007
月份10
日期30
卷號104
期次44
出版社National Academy of Sciences
出版地United States
頁次17266 - 17271
國際標準期刊號0027-8424
語言英式英語
關鍵詞Dynamic covalent chemistry, Molecular recognition, Polyrotaxanes, Self-assembly, Template-directed synthesis

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