Helicenes Grafted with 1,1,4,4-Tetracyanobutadiene Moieties: π-Helical Push-Pull Systems with Strong Electronic Circular Dichroism and Two-Photon Absorption

Chemistry. 2018 Sep 25;24(54):14484-14494. doi: 10.1002/chem.201802763. Epub 2018 Sep 3.

Abstract

Enantiopure P- and M-carbo[6]helicenes substituted with one or two tetracyanobutadiene moieties at positions 2 and 15 have been prepared. Grafting of these electron-accepting groups onto the π-helical core resulted in strong charge-transfer effects, which greatly affected the UV/Vis, electronic circular dichroism (ECD), and two-photon absorption (TPA) responses. The ECD signal was found to be reversibly switched by applying a redox stimulus.

Keywords: charge transfer; chiroptical activity; helicenes; tetracyanobutadiene; two-photon absorption.