Novel Isoindigo-Based Organic Semiconductors End Capped with 1,1-Dicyanomethylene-3-Indanone: Effect of the Bromination and Position of Bromine Substituents on the Chemical–Physical and Electrical Properties

We report here on the synthesis and characterization of three novel isoindigo (II)-based organic semiconductors. The three dyes are based on an electron acceptor II core, symmetrically linked to two 3-octylthiophene donor rings; this common fragment, easily synthesizable, is end-capped with three different auxiliary electron acceptor groups, 1,1-Dicyanomethylene-3-Indanone (<b>IDM</b>) and two derivatives of it, bearing a bromine atom in position 5 or 6 of the <b>IDM</b> ring. The effect of the bromination and of the position of the bromine atom on the chemical-physical and electrical properties of the compounds were examined by means of thermal, optical, and electrochemical analysis; the electronic properties were investigated in more details at the DFT level. The novel compounds were used as active layers in organic field effect transistors: all the II derivatives were n-type unipolar semiconductors with electron mobilities ranging between 10^-3 and 10^-4 cm²/V∙s.