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https://doi.org/10.1039/c001343a
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. https://doi.org/10.1039/c001343a | 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 | URI: | http://scholarbank.nus.edu.sg/handle/10635/76041 | ISSN: | 14770520 | DOI: | 10.1039/c001343a |
Appears in Collections: | Staff Publications |
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