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Facile Synthesis of Thienopyrroledione-Based π-Conjugated Polymers via Direct Arylation Polycondensation under Aerobic Conditions

Ichige, Akito, Saito, Hitoshi, Kuwabara, Junpei, Yasuda, Takeshi, Choi, Jun-Chul, Kanbara, Takaki
Macromolecules 2018 v.51 no.17 pp. 6782-6788
additives, aerobic conditions, air, arylation, catalysts, catalytic activity, condensation reactions, light emitting diodes, molecular weight, palladium, photoluminescence, polymers, solar energy, solvents
An exploration of the tolerance of a Pd-catalyzed direct arylation polycondensation under aerobic conditions was carried out. The polycondensation of 5-(2-ethylhexyl)thieno-[3,4-c]-pyrrole-4,6-dione with 2,7-dibromo-9,9-dioctylfluorene was accomplished smoothly in air by refluxing the solvents, without the need for additional catalysts or additives. This simple modification allowed the use of commercially available reagent-grade solvents without further purification and produced the corresponding π-conjugated polymer with a molecular weight and yield comparable to those obtained under conventional oxygen- and moisture-free conditions. The facile synthetic protocol was applicable to the synthesis of other thienopyrroledione-based π-conjugated polymers. The obtained polymers served as semiconducting materials in organic light-emitting diodes (OLEDs) and organic photovoltaics. The effects of the terminal structure of the polymer on its photoluminescence and OLED device characteristics were also evaluated.