“Click”-functionalization of conducting poly(3,4-ethylenedioxythiophene) (PEDOT)

Abstract

Efficient post-functionalization of conductive polymer films was achieved by Cu(+)-catalyzed "click"-cycloaddition of novel poly(azidomethyl-EDOT) and various functionalized terminal alkynes under mild heterogeneous conditions with high conversion efficiencies.

Label-free electrochemical DNA sensor using “click”-functionalized PEDOT electrodes

“…Compared to these measurements, the current intensity for bare gold electrodes tested in electrolyte solution free of monomer (100 mM TBAPF 6 in DCM) was very low. After addition of the azido-EDOT monomer to the electrolyte, a large current increase was observed at around 1 V, corresponding to the polymerization of the monomer, as reported by Bu et al (2008). In the second polymerization scan, a new irreversible redox wave was detected in the low-potential region, indicating the deposition of azido-PEDOT on the gold electrode.…”

“…Azidomethyl-substituted 3,4-ethylenedioxythiophene (azido-EDOT) was synthesized following the protocol developed by Bu et al (2008). 99.8% anhydrous dichloromethane (DCM) and tetrabutylammonium hexafluorophosphate (TBAPF6) were supplied by Sigma-Aldrich Co. (USA).…”

“…reported the first example of post-functionalization of a novel conducting poly (azidomethyl-EDOT) (azido-PEDOT) by "click" chemistry with various types of terminal alkynes (Bu et al, 2008). Since then, several examples of derivatization of azido-PEDOT with alkyne-containing fluorophores (Daugaard et al, 2008), ferrocene, glycosides, or fullerenes (Bu et al, 2011) have been described.…”

“…PEDOT was selected as CP due to the simplicity of EDOT monomer functionalization and to its high electrochemical stability (Bu et al, 2008;Kros et al, 2005). An acetylene-terminated oligonucleotide probe, complementary to a HCV target sequence, was immobilized onto an azido-PEDOT polymer by covalent binding using "click" chemistry.…”

Spatially Selective Functionalization of Conducting Polymers by “Electroclick” Chemistry

“…[10,11] This is one of the most widely applied reactions in the area of ''click chemistry'', as defined by Sharpless and coworkers. [12] Other authors independently and in parallel reported on the electropolymerization of PEDOT-N 3 , [13] and on synthesis and polymerization of azide-functionalized polypyrrole. [14] In our previous report, we showed that PEDOT-N 3 films can be functionalized with various alkyne-containing molecules, yielding conducting polymer films with new optical (fluorescent) or physical properties (engineered surface free energy).…”