Chiroptical Switching in an Enantiomeric Pair of Binaphthylenes Based on Redox-Active 1,8-Naphthalimide Substituents

Molecules whose chiroptical signal can be controllably and reversibly altered are of great interest in emerging optoelectronic technologies. Here, we outline the synthesis of a pair of chiral enantiomers (S)-1,1′-binaphthalene-2,2′-bis(1,8-naphthalimide) and (R)-1,1′-binaphthalene-2,2′-bis(1,8-naphthalimide) and their characterization with a range of structural, electrochemical, and spectroelectrochemical techniques. We show that reduction of the naphthalimide moieties in each enantiomer causes substantial changes in their optical and chiroptical properties, enabling them to perform as highly sensitive and reversible redox-modulated chiroptical switches.