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Five new copolymers based on the anthanthrone moiety were synthesized using Stille coupling. The anthanthrone unit was coupled with two electron-rich units (thiophene and carbazole) and three electron-poor units (thienopyrroledione, diketopyrrolopyrrole, and benzothiadiazole). The optoelectronics properties of the polymers were investigated and suggest that the anthanthrone moiety dictates the electronic properties of the materials with little regards to the nature of the comonomers. Fluoride-promoted photoinduced electron transfer on anthanthrone derivatives yielded to radical anion species that can be reversibly oxidized to the neutral form by exposure to air.

Anthanthrone and its derivatives are large polycyclic aromatic compounds (PACs) that pose a number of challenges for incorporation into the structure of soluble conjugated polymers. For the first time, this group of PACs was employed as the building blocks for the synthesis of copolymers (P1–P5) based on poly[(arylene ethynylene)-alt-(arylene vinylene)]s backbone (−Ph–C≡C–Anth–C≡C–Ph–CH=CH–Ph–CH=CH−)n. During the synthesis of P1–P5, different alkyloxy side chains were incorporated in order to tune the properties of the polymers. Of the copolymer series only P1 (containing anthanthrone and branched 2-ethylhexyloxy side chains on phenylenes), P2 and P3 (for which the anthanthrones containing carbonyl groups were converted to anthanthrene containing alkyloxy substituents) were soluble. The photophysical, electrochemical, electroluminescent and photovoltaic properties of P1–P3 are reported, compared and discussed with respect to the effects of side chains.