Abstract
A convenient and efficient deiodination polycondensation method for the synthesis of dioxypyrrole-based (XDOP) polymers is reported. N-Halosuccinimides, iodine, and bromine were evaluated as halogenating agents to produce 2,5-halodioxypyrroles in situ via halodecarboxylation of 3,4-dioxypyrrole-2,5-dicarboxylic acids, which were then polymerized at 60 °C using dichloromethane or chloroform as solvent. When iodine and N-iodosuccinimide were employed as electrophilic halogen sources, the methodology produced macromolecules (Mn = 6.2–22.9 kDa) in satisfactory yields (55–71%) for two N-alkyl-3,4-dialkyloxypyrrole-based monomers that were tested. This method can be employed to produce a variety of XDOP-based homopolymers and regioregular copolymers starting from discrete oligomers under relatively mild reaction conditions.
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