Efficient post-polymerization functionalization of conducting poly(3,4-ethylenedioxythiophene) (PEDOT) via 'click'-reaction

The possibility to functionalize polymers after a successful polymerization process is often an important challenge in macromolecular science. Herein, modified electrodes based on azide-containing potentio-dynamically electropolymerized PEDOT derivatives are reported. This reactive coatings are subsequently modified under mild heterogeneous conditions by copper-catalyzed Huisgen 1,3-dipolar cycloaddition with terminal alkynes, the so-called 'click'-reaction. A series of terminal alkynes have been successfully used for the facile immobilization of neutral, electron-accepting and electron-donating units to the conducting PEDOT with high conversion efficiencies showing the broad scope of the strategy. The route is devoid of the limitations generated by the various steric and electronic impacts of the substituents when attached to the monomer before polymerization. (C) 2010 Elsevier Ltd. All rights reserved.