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Conducting materials prepared by the oxidation of <Emphasis Type="Italic">p</Emphasis>-phenylenediamine with <Emphasis Type="Italic">p</Emphasis>-benzoquinone |
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| Authors: | |
| Institution: | 1.Institute of Macromolecular Chemistry,Academy of Sciences of the Czech Republic,Prague 6,Czech Republic;2.Faculty of Mathematics and Physics,Charles University in Prague,Prague 8,Czech Republic;3.Linz Institute for Organic Solar Cells/Institute of Physical Chemistry,Johannes Kepler University of Linz,Linz,Austria;4.University of Würzburg and Bavarian Centre for Applied Energy Research (ZAE Bayern),Würzburg,Germany;5.Polymer Electronics Research Centre and NMR Centre, School of Chemical Sciences,The University of Auckland,Auckland,New Zealand |
| Abstract: | p-Phenylenediamine was oxidized with p-benzoquinone in the aqueous solutions of methanesulfonic acid (MSA). The conductivity of the products increased with increasing concentration of MSA from 1.5?×?10?12 S cm?1 in 0.1 M MSA up to 3.4?×?10?4 S cm?1 in 5 M MSA. The low-molecular-weight products are basically composed of one p-benzoquinone and two p-phenylenediamine molecules. Their molecular structure is discussed on the basis of mass, Fourier-transform infrared, Raman, NMR and electron paramagnetic resonance (EPR) spectroscopies. The formation of 2,5-di(p-phenylenediamine)-p-benzoquinone protonated with methanesulfonic acid best complies with the information provided by spectroscopic techniques. Its conversion to hydroquinone tautomer explains the formation of unpaired spins observed by EPR and their potential contribution to the conduction. |
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