Redox-Dependent Conformational Switching of Diphenylacetylenes

Abstract

Herein we describe the design and synthesis of a redox-dependent single-molecule switch. Appending a ferrocene unit to a diphenylacetylene scaffold gives a redox-sensitive handle, which undergoes reversible one-electron oxidation, as demonstrated by cyclic voltammetry analysis. 1H-NMR spectroscopy of the partially oxidized switch and control compounds suggests that oxidation to the ferrocenium cation induces a change in hydrogen bonding interactions that results in a conformational switch.

Keywords

• molecular switch
• ferrocene
• hydrogen bonding
• amide bond
• redox
• translational isomerism