Hole-Transporting Materials based on Oligo(hetero)aryls with a Naphthodithiophene Core - Succinct Synthesis by Twofold Direct C-H Olefination

Abstract

This work demonstrated the first synthetic application of direct C-H olefinations in the step-saving preparation of various hole-transporting materials (HTM) for efficient perovskite solar cells (PSC). Cross-dehydrogenative couplings of naphthodithiophene (NDT) with vinyl arenes under palladium-catalysis facilely generated various new oligo(hetero)aryls with internal alkenes. Reaction conditions were optimized, which gave the product isolated yields of up to 71 % with high (E)-stereoselectivity. These readily accessible NDT core-based small molecules involving olefin as π-spacers displayed immediate power conversion efficiencies of up to 17.2 % without a device oxidation process that is required for the commercially available spiro-OMeTAD and most other existing HTMs while fabricated in corresponding PSC devices.

Keywords: Direct C−H Olefination; Hole-Transporting Material; Naphthodithiophene; Perovskite Solar Cell; Synthesis Design.