American Chemical Society
ja409006y_si_002.cif (52.25 kB)

A Water-Soluble pH-Triggered Molecular Switch

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posted on 2013-11-27, 00:00 authored by Sergio Grunder, Psaras L. McGrier, Adam C. Whalley, Megan M. Boyle, Charlotte Stern, J. Fraser Stoddart
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 1H 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.