Coupling of the Decarboxylation of 2-Cyano-2-phenylpropanoic Acid to Large-Amplitude Motions: A Convenient Fuel for an Acid-Base-Operated Molecular Switch

The decarboxylation of 2-cyano-2-phenylpropanoic acid is fast and quantitative when carried out in the presence of 1?molar equivalent of a [2]catenane composed of two identical macrocycles incorporating a 1,10-phenanthroline unit in their backbone. When decarboxylation is over, all of the catenane molecules have experienced large-amplitude motions from neutral to protonated catenane, and back again to the neutral form, so that they are ready to perform another cycle. This study provides the first example of the cyclic operation of a molecular switch at the sole expenses of the energy supplied by the substrate undergoing chemical transformation, without recourse to additional stimuli. Poetry in motion: Carboxylic acid 1 was found to be a convenient fuel for the operation of a molecular switch that moves under the influence of protonation-deprotonation steps. The cyclic motions of the catenane switch were induced solely by the chemical energy supplied by the decarboxylation of 1, without recourse to additional stimuli.