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Issue 11, 2010
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Efficient synthesis of a hetero[4]rotaxane by a “threading-stoppering-followed-by-clipping” approach

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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.

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

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Article information


Submitted
21 Jan 2010
Accepted
23 Mar 2010
First published
08 Apr 2010

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

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

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