Tailoring helical ends of π-extended [6]heterohelicenes to control optical, and electrochemical features

Abstract

The inherent helical chirality and improved π-stacking capabilities endow helicenes with fascinating photophysical characteristics when decorated with lateral π-extensions. Here, we report the synthesis and physicochemical characterization of expanded hetero[6]helicenes fused with thiadiazole and selenadiazole rings at the helical ends. Comparing these heterohelicenes revealed the impact of the heteroatom-embedded aromatic rings on the excited state and redox features. A small structural variation of the terminal rings from thiadiazole to selenadiazole caused a striking change in the heterohelical nanographenes.