Alternative charge stabilisation and a changing reactivity of 1,3,5-triazine based starburst compounds as studied by in situ ESR/UV–vis–NIR spectroelectrochemistry |
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Authors: | Peter Rapta Krzysztof R Idzik Vladimír Lukeš Rainer Beckert Lothar Dunsch |
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Institution: | 1. Center of Spectroelectrochemistry, Electrochemistry and Conducting Polymers Department, Leibniz-Institute for Solid State and Materials Research, D-01171 Dresden, Germany;2. Department of Physical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinskeho 9, SK-81237 Bratislava, Slovak Republic;3. Institute of Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstraße 10, 07743 Jena, Germany;4. Department of Chemistry, Faculty of Medicinal Chemistry and Microbiology, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland |
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Abstract: | The role of the chemical structure in an alternative charge stabilisation and a changing reactivity of star-shaped compounds with a central triazine ring linked to aryl groups like thiophene, furan or ethylenedioxythiophene synthesized by a Stille cross-coupling procedure, is followed by spectroelectrochemical measurements. While cathodic reduction leads to stable anion radicals with a delocalised spin on the central triazine moiety, dimerisation and oligomerisation occurs upon anodic oxidation. The stability of the charged states in the polymer film increased substantially using an EDOT (3,4-ethylenedioxythiophene) side group. The location of the charged states on the molecules has been proved by computations. These star-shaped molecules are excellent model structures for studies of the competition of dimerisation and oligomerisation processes based on the variation of the electron and spin distribution in the molecules. |
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