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Title: Efficient synthesis of a hetero[4]rotaxane by a threading-stoppering- followed-by-clipping approach
Authors: Yin, J. 
Chi, C. 
Wu, J. 
Issue Date: 2010
Citation: Yin, J., Chi, C., Wu, J. (2010). Efficient synthesis of a hetero[4]rotaxane by a threading-stoppering- followed-by-clipping approach. Organic and Biomolecular Chemistry 8 (11) : 2594-2599. ScholarBank@NUS Repository.
Abstract: A "threading-stoppering-followed-by-clipping" approach was used for the synthesis of a hetero[4]rotaxane, in which one cucurbit[6]uril (CB[6]) and two hetero crown ether macrocycles are threaded onto one dumbbell-shaped molecule. The process involves three steps: (1) threading of a CB[6] macrocycle onto a thread containing two dialkylammonium sites to form a CB[6]-based pseudo[2]rotaxane; (2) stoppering of the as-formed pseudo[2]rotaxane by imine condensation reaction followed by reduction/protonation to afford a CB[6]-based [2]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 hetero[4]rotaxane in good yield. The whole process was followed by NMR spectroscopy and the structure of the hetero[4]rotaxane was confirmed by NMR spectroscopy, elemental analysis and mass spectrometry. © The Royal Society of Chemistry 2010.
Source Title: Organic and Biomolecular Chemistry
ISSN: 14770520
DOI: 10.1039/c001343a
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