Ethylenedioxypyrrole EDOP and Its Derivatives

The first synthesis of a 3,4-dialkoxypyrrole (3,4-dimethoxypyrrole) was published by Merz et al. The EDOT analog3,4-ethylenedioxypyrrole (EDOP) soon followed,and its poly(styrenesulfonic acid) complex PEDOPrPSS analog to PEDOT PSS was claimed in a patent 1996.  

The synthetic routes to the monomeric EDOP and similar compounds are roughly outlined in Pigure 13.21, following the Reynolds and Walczak review, where more detailed comments can be found.  

R = Alkyl, Benzyl, Alkanesulfonyl, Alkoxy, Allyl X = Dialkyl or Alkylene 

Synthetic routes to XDOPs. (Data from R. M. Walczak and J. R. Reynolds, 2006, Adz Mater 18(9) 1121-1131.) 

The PXDOPs are unique in combining low oxidation potential, as a result from the alkylenedioxy moiety and similar to PEDOT, with middle to high band gap resulting from the electron-rich pyrrole moiety. 

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