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J Am Chem Soc. 2013 Nov 27;135(47):17691-4. doi: 10.1021/ja409006y. Epub 2013 Nov 18.

A water-soluble pH-triggered molecular switch.

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Department of Chemistry, Northwestern University , 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States.


A bistable donor-acceptor [2]catenane, which is composed of a crown ether containing a hydroquinone unit and a 1,5-diaminonaphthalene unit, interlocked mechanically by cyclobis(paraquat-p-phenylene) as its tetrachloride, exists as a mixture of translational isomers, both in the solid state and in aqueous solution. UV/vis and (1)H NMR spectroscopies demonstrate that this isomeric mixture can be switched in water in the presence of hydrochloric acid to afford a single diprotonated derivative in which only the hydroquinone unit resides inside the cavity of the tetracationic cyclophane. Treatment with 1,4-diazabicyclo[2.2.2]octane resets the molecular switch.


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