Catalytic Reversible (De)hydrogenation To Rotate a Chemically Fueled Molecular Switch. (15th November 2022)

• Record Type: Journal Article
• Authors: Olivieri, Enzo; Shao, Na; Rosas, Roselyne; Naubron, Jean‐Valère; Quintard, Adrien
• Is Part Of: Angewandte Chemie. Volume 134:Number 50(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-11-15
• Subjects: Catalysis -- Conformation -- Green Chemistry -- Hydrogenation -- Molecular Switch; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202214763
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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. Abstract : Most chemically fueled molecular switches suffer from the problem of waste accumulation inhibiting the system. Herein, we present a 180° rotating molecular switch based on reversible (de)hydrogenation avoiding waste accumulation. Catalyzed by an iridium complex, switching from a pressure of argon to a pressure of hydrogen triggers a reversible change in the system from alcohol to ketone, promoting the rotation around an alkyne axis.