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Reactive Groups On Polymer-Covered Electrodes. 5. Synthesis And Cyclovoltammetric Analysis Of 3-Substituted Thiophene Derivatives†

H. Welzel, G. Kossmehl, H. Boettcher, G. Engelmann, W. Hunnius
Published 1997 · Chemistry

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Various functionalized polythiophene films on electrode surfaces were produced by electropolymerization. Starting from 3-(2-hydroxyethyl)thiophene (1) different ether and ester derivatives were synthesized:  3-(2-(benzyloxy)ethyl)thiophene (2), 3-[2-((triphenylmethyl)oxy)ethyl]thiophene (3), 3-[2-((trimethylsilyl)oxy)ethyl]thiophene (4), 3-[2-((dimethyl-tert-butylsilyl)oxy)ethyl]thiophene (5), 3-(2-acetoxyethyl)thiophene (6), 3-(2-(benzoyloxy)ethyl)thiophene (7), 3-[2-((p-nitrobenzoyl)oxy)ethyl]thiophene (8), and 3-[2-((3,5-dinitrobenzoyl)oxy)ethyl]thiophene (9). Cyclovoltammetric analyses in acetonitrile with tetrabutylammonium perchlorate (TBAP) as supporting electrolyte gave the characteristic peak potentials (Ep's) of the electrochemical oxidation of these monomers. Under our standard conditions homopolymerization of the monomers 2−9 could not be achieved, whereas copolymerization of 2−9 with 3-methylthiophene (10) was successful. The resulting polymeric films were characterized by FT IR spectroscopy ...



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