A luminescent molecular turnstile

Abstract

A molecular turnstile 1 based on a hydroquinone luminescent hinge bearing two divergently oriented pyridyl units behaving as a rotor and equipped with a handle composed of a tridentate coordinating site considered as the stator was synthesized and its structure was studied in the solid state by X-ray diffraction on single crystal. Its dynamic behaviour in solution was investigated by 1- and 2-D NMR experiments which revealed the free rotation of the rotor around the stator. The rotational movement was locked upon addition of Pd(II) simultaneously complexed by the tridentate moiety of the stator and one of the two monodentate pyridyl sites of the rotor. Interestingly, whereas the open state of the turnstile was luminescent, for its closed state the emission was quenched by the heavy atom effect of Pd(II).