New conducting polymers functionalized with redox-active tetrazines

We describe the synthesis of two new polymerizable monomers, based on respectively one thiophene-pyrrole-thiophene (SNS) moiety and one carbazole moiety, both functionalized by 3-chloro-6-alkoxy-s-tetrazine pendant groups. The electrochemical response of the monomers and the subsequent polymers has been studied both by cyclic voltametry and UV-visible spectroscopy. In both case conducting polymers are obtained, featuring both the redox activity of the main chain in oxidation and of the tetrazine functional group upon reduction, but only the one stemming from the SNS moiety is stable to cycling. The spectroscopic and electrochemical characteristics of both the monomer and the polymer are detailed herein, and especially a stable film has been obtained on an ITO plate. (C) 2011 Elsevier B.V. All rights reserved.