Catalytic Reversible (De)hydrogenation To Rotate a Chemically Fueled Molecular Switch

Enzo Olivieri (1) , Na Shao (1) , Roselyne Rosas (2) , Jean‐valère Naubron (2) , Adrien Quintard (1, 3)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 FRSCM - Fédération des Sciences Chimiques de Marseille
3 DCM - Département de Chimie Moléculaire

We report here the development of a rotating molecular switch based on metal-catalyzed reversible (de)-hydrogenation. Under an argon atmosphere, acceptorless dehydrogenation induces a switch from an alcohol to a ketone, while reversing to a hydrogen pressure switches back the system to the alcohol. Based on a tolane scaffold, such reversible (de)-hydrogenation enables 180°rotation. The absence of waste accumulation in a switch relying on chemical stimuli is of great significance and could potentially be applied to the design of efficient complex molecular machines.

Keywords: molecular switch; catalysis; supramolecular; hydrogenation

Domains: Chemical Sciences; Organic chemistry

Enzo Olivieri, Na Shao, Roselyne Rosas, Jean‐valère Naubron, Adrien Quintard. Catalytic Reversible (De)hydrogenation To Rotate a Chemically Fueled Molecular Switch. Angewandte Chemie International Edition, 2022, 61 (50), ⟨10.1002/anie.202214763⟩. ⟨hal-03955415⟩