Synthesis of a pH-Sensitive Hetero[4]Rotaxane Molecular Machine that Combines [c2]Daisy and [2]Rotaxane Arrangements

Philip Waelès (1) , Benjamin Riss-Yaw (1) , Frédéric Coutrot (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

The synthesis of a novel pH-sensitive hetero[4]rotaxane molecular machine through a self-sorting strategy is reported. The original tetra-interlocked molecular architecture combines a [c2]daisy chain scaffold linked to two [2]rotaxane units. Actuation of the system through pH variation is possible thanks to the specific interactions of the dibenzo-24-crown-8 (DB24C8) macrocycles for ammonium, anilinium, and triazolium molecular stations. Selective deprotonation of the anilinium moieties triggers shuttling of the unsubstituted DB24C8 along the [2]rotaxane units.

Mots clés: daisy chain; molecular devices; biomimetic synthesis; rotaxane synthesis; template synthesis

Domaines: Chimie organique

Philip Waelès, Benjamin Riss-Yaw, Frédéric Coutrot. Synthesis of a pH-Sensitive Hetero[4]Rotaxane Molecular Machine that Combines [c2]Daisy and [2]Rotaxane Arrangements. Chemistry - A European Journal, 2016, 22, pp.6837-6845. ⟨10.1002/chem.201600453⟩. ⟨hal-01321373⟩