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Org Lett. 2007 Dec 20;9(26):5553-6. Epub 2007 Nov 30.

Benzo-21-crown-7/secondary dialkylammonium salt [2]pseudorotaxane- and [2]rotaxane-type threaded structures.

Author information

1
Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China.

Abstract

We demonstrate that secondary dialkylammonium salts can thread through the cavity of benzo-21-crown-7 to form [2]pseudorotaxanes with binding constants (527-1062 M-1 in acetone) higher than the corresponding values (135-261 M-1 in acetone) of the analogous complexes with their traditionally used host, dibenzo-24-crown-8. Based on this new benzo-21-crown-7/secondary dialkylammonium salt recognition motif, a [2]rotaxane was successfully prepared. The formation of these threaded structures was confirmed by proton NMR spectroscopy, electrospray ionization mass spectrometry, and X-ray single crystal analysis.

PMID:
18047364
DOI:
10.1021/ol702510c

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