Synthesis of furo[3,2-b:4,5-b']diindoles and their optical and electrochemical properties.

An efficient two-step palladium catalyzed synthesis of furo[3,2-b:4,5-b']diindoles, a hitherto unknown symmetrical heterocyclic core structure, was developed. The synthesis is based on a regioselective Suzuki-Miyaura cross coupling reaction of tetrabromofuran and subsequent double N-arylation. Selected compounds were studied with regard to their optical and electrochemical properties. The compounds show fluorescence with high quantum yields and non-reversible oxidation events. The compounds possess similar HOMO-LUMO band gaps compared to their sulfur and nitrogen analogs. Variation of the substituents hardly affects the HOMO-LUMO gap, but allows for some fine-tuning of the electron affinity and ionization potential as well as quantum yields. The compounds prepared represent interesting candidates for the development of organic electronic materials.