POLY(ARYLENE-ALT-[BIS(1-METHYLPYRROLYLENE)])S .1. SYNTHESIS AND ELECTROCHEMICAL POLYMERIZATION OF TERARENES

Novel alternating conjugated copolymers were prepared by electrochemic al polymerization of defined bis(1-methylpyrrol-2-yl)arenes. The comon omers were synthesized by the nickel-catalyzed coupling reaction (Kuma da synthesis) of 1-methylpyrrol-2-yl anion with various dibromoarenes. The monomers were characterized via common techniques, such as ultrav iolet/visible (UV/Vis), proton nuclear magnetic resonance (H-1 NMR), C -13 NMR, infrared (IR) and mass spectroscopy (MS). All monomers show i rreversible electrochemical behavior and could therefore be polymerize d to conducting polymers. The resulting copolymers reveal a conductivi ty in the range of 10(-2) S/cm to less than 10(6) S/cm. The conductivi ty mainly depends on steric hindrance between the aromatic rings. A hi gh decoupling of the conjugated systems could be observed in case of t he anthracene/bis(1-methylpyrrole) copolymer, which is due to the high est torsion angle between the rings of the series. Additionally, in th e case of the furan derivative a soluble copolymer is formed under cer tain conditions in the reduced state.