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Chemistry. 2013 Jul 1;19(27):8850-60. doi: 10.1002/chem.201300049. Epub 2013 May 15.

Using "threading followed by shrinking" to synthesize highly stable dialkylammonium-ion-based rotaxanes.

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1
Department of Chemistry and Center for Emerging Material and Advanced Devices, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei, Taiwan 10617, R.O.C.

Abstract

Herein, we report a "threading followed by shrinking" approach for the synthesis of rotaxanes by using an "oxygen-deficient" macrocycle that contained two arylmethyl sulfone units and the dumbbell-shaped salt bis(3,5-dimethylbenzyl)ammonium tetrakis(3,5-trifluoromethylphenyl)borate as the host and guest components, respectively. The extrusion of SO2 from both of the arylmethyl sulfone units of the macrocyclic component in the corresponding [2]pseudorotaxane resulted in a [2]rotaxane that was sufficiently stable to maintain its molecular integrity in CD3 SOCD3 at 393 K for at least 5 h.

PMID:
23677595
DOI:
10.1002/chem.201300049
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