New monomer based on thienopyrazine with fluorocarbazole substituents as a promising building block for organic electronics

Abstract

A new monomer, 2,3-bis[6-fluoro-9-(2-octyldodecyl)-9H-carbazol-3-yl]-3,3'-[5,7-di(5-bromothienyl-2)thieno[3,4-b]pyrazine, M1, based on thienopyrazine containing fluorocarbazole substituents in the pyrazine ring has been synthesized. The structure of the compound has been proved by ¹H and ¹³C NMR and elemental analysis. The HOMO and LUMO energies for monomer M1 and its precursor 3 determined by the electrochemical method are–5.03 and–3.31 eV, as well as–5.28 and–3.36 eV, respectively. Band gap widths E_g^ec are 1.72 and 1.92 eV for compounds M1 and 3, respectively. The new structural fragment has rather deep energy levels of frontier molecular orbitals and a small band gap width; therefore, it is a promising building block for the synthesis of polymers for organic electronics.