Double [4]Helicene-like Naphthobisbenzothiophene Diimides and Their Thienyl-S,S-dioxidized Derivatives with Attractive Solid-State Fluorescence and High Electron Affinity.

A series of double [4]helicene-like naphthobisbenzothiophene diimides and their thienyl-S,S-dioxidized derivatives are synthesized via MoCl-catalyzed cyclization and -CPBA-mediated oxidation reactions. The functional five-membered ring diimides show a helicene-like geometry, strong solid-state fluorescence, and deep LUMO of -4.37 eV.