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|Title:||Efficient synthesis of a heterorotaxane by a threading-stoppering- followed-by-clipping approach|
|Authors:||Yin, J. |
|Source:||Yin, J., Chi, C., Wu, J. (2010). Efficient synthesis of a heterorotaxane by a threading-stoppering- followed-by-clipping approach. Organic and Biomolecular Chemistry 8 (11) : 2594-2599. ScholarBank@NUS Repository. https://doi.org/10.1039/c001343a|
|Abstract:||A "threading-stoppering-followed-by-clipping" approach was used for the synthesis of a heterorotaxane, in which one cucurbituril (CB) and two hetero crown ether macrocycles are threaded onto one dumbbell-shaped molecule. The process involves three steps: (1) threading of a CB macrocycle onto a thread containing two dialkylammonium sites to form a CB-based pseudorotaxane; (2) stoppering of the as-formed pseudorotaxane by imine condensation reaction followed by reduction/protonation to afford a CB-based rotaxane with two new dialkylammonium sites; and (3) selective clipping of two hetero crown ether macrocycles onto the newly-formed ammonium sites and subsequent reduction of the imine bonds in each crown ether to afford the final heterorotaxane in good yield. The whole process was followed by NMR spectroscopy and the structure of the heterorotaxane was confirmed by NMR spectroscopy, elemental analysis and mass spectrometry. © The Royal Society of Chemistry 2010.|
|Source Title:||Organic and Biomolecular Chemistry|
|Appears in Collections:||Staff Publications|
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