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Two novel indacenodithiophene (IDT) based donor–acceptor conjugated polymers for use in organic field effect transistors and photovoltaic devices are synthesized and characterized. The effect of inclusion of two fluorine atoms on the acceptor portion of the polymer is thoroughly investigated via a range of techniques. The inductively withdrawing and mesomerically donating properties of the fluorine atoms result in a decrease of the highest occupied molecular orbital (HOMO), with little effect on the lowest unoccupied molecular orbital (LUMO) as demonstrated through density functional theory (DFT) analysis. Inclusion of fluorine atoms also leads to a potentially more planar backbone through inter and intrachain interactions. Use of the novel materials in organic field effect transistor (OFET) and organic photovoltaic (OPV) devices leads to high mobilities around 0.1 cm²/(V s) and solar cell efficiencies around 4.5%.