1489246-68-5Relevant articles and documents
A water-soluble pH-triggered molecular switch
Grunder, Sergio,McGrier, Psaras L.,Whalley, Adam C.,Boyle, Megan M.,Stern, Charlotte,Stoddart, J. Fraser
, p. 17691 - 17694 (2013)
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.