Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.

Issue 11, 2010
Previous Article Next Article

Efficient synthesis of a hetero[4]rotaxane by a “threading-stoppering-followed-by-clipping” approach

Author affiliations


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.

Graphical abstract: Efficient synthesis of a hetero[4]rotaxane by a “threading-stoppering-followed-by-clipping” approach

Back to tab navigation

Supplementary files

Article information

21 Jan 2010
23 Mar 2010
First published
08 Apr 2010

Org. Biomol. Chem., 2010,8, 2594-2599
Article type

Efficient synthesis of a hetero[4]rotaxane by a “threading-stoppering-followed-by-clipping” approach

J. Yin, C. Chi and J. Wu, Org. Biomol. Chem., 2010, 8, 2594
DOI: 10.1039/C001343A

Social activity

Search articles by author