Synthesis of n-type semiconducting polymer consisting of benzodipyrrolidone and thieno-[3,4-c]-pyrrole-4,6-dione via CH direct arylation

•Benzodipyrrolidone(BDP)-based conjugated polymer was prepared by direct arylation polycondensation.•Introduction of the BDP unit into the polymer resulted in the n-type semiconducting characteristics.•Direct arylation polycondensation should provide practical access to various semiconducting materials in organic optoelectronic devices.

Direct arylation polycondensation of 3,​7-​bis(4-​bromophenyl)​-​1,​5-​bis(2-​octyldodecyl)​benzo[1,​2-​​b:4,​5-​b']​dipyrrole-​2,​6(1H,​5H)​-​dione with 5-(2-ethylhexyl)-thieno-[3,4-c]-pyrrole-4,6-dione gave the corresponding benzodipyrrolidone-based conjugated polymer with a molecular weight of 147,000 in 92% yield. The optical and thermal properties of the polymer were evaluated. The polymer showed n-type semiconducting behavior in organic field-effect transistors with an electron mobility of 1.3 ± 0.2 × 10−3 cm2 V−1 s−1.

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