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Poly{arylene‐ alt ‐[bis(1‐methylpyrrolylene)]}s, 1. Synthesis and electrochemical polymerization of terarenes

1996; Wiley; Volume: 197; Issue: 8 Linguagem: Inglês

10.1002/macp.1996.021970819

1521-3935

Uwe Geißler, Manfred L. Hallensleben, Nils Rohde,

Porphyrin and Phthalocyanine Chemistry

Abstract Novel alternating conjugated copolymers were prepared by electrochemical polymerization of defined bis(1‐methylpyrrol‐2‐yl)arenes. The comonomers were synthesized by the nickel‐catalyzed coupling reaction (Kumada synthesis) of 1‐methylpyrrol‐2‐yl anion with various dibromoarenes. The monomers were characterized via common techniques, such as ultraviolet/visible (UV/Vis), proton nuclear magnetic resonance ( 1 H NMR), 13 C NMR, infrared (IR) and mass spectroscopy (MS). All monomers show irreversible electrochemical behavior and could therefore be polymerized to conducting polymers. The resulting copolymers reveal a conductivity in the range of 10 ‐2 S/cm to less than 10 ‐6 S/cm. The conductivity mainly depends on steric hindrance between the aromatic rings. A high decoupling of the conjugated systems could be observed in case of the anthracene/bis(1‐methylpyrrole) copolymer, which is due to the highest torsion angle between the rings of the series. Additionally, in the case of the furan derivative a soluble copolymer is formed under certain conditions in the reduced state.