Chemical stability of conducting polymers: Friedel-Crafts reactions of alcohols with poly(3,4-ethylenedioxythiophene) (PEDOT)

The conducting polymer poly(3,4-ethylenedioxythiophene) (PEDOT) facilitates a Friedel-Crafts reaction between benzylic or allylic alcohols and benzene or toluene, giving the arene and water as a by-product. Aliphatic alcohols gave poorer yields of coupling product, and elimination to the corresponding alkene is a competitive process in many cases. The results are consistent with an acid-catalyzed Friedel-Crafts reaction, although we have not determined the mechanism with respect to the polymer as yet. However, it is clear that PEDOT facilitates this reaction, and the formation of water as a by-product may have implications in its commercial applications.