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Oxidation of rubrene, and implications for device stability

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Abstract

The rapid spontaneous photo-oxidation of rubrene to form endo-peroxide, rubrene-Ox1, was monitored via 1H NMR and UV-vis spectroscopy. The reaction is thermally reversible, which restores high mobility devices in both the crystalline thin film and single crystal. Prolonged stirring in chlorinated solvents yields a secondary, irreversible product, rubrene-Ox2, which has lost phenol, as confirmed by single crystal analysis. An acid-catalyzed rearrangement of the endo-peroxide to form rubrene-Ox2 was identified here with Density Functional Theory (DFT). Implications of the nature of these processes for the preparation of organic transistors are described.

Graphical abstract: Oxidation of rubrene, and implications for device stability

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Publication details

The article was received on 15 Dec 2017, accepted on 12 Jan 2018 and first published on 15 Jan 2018


Article type: Paper
DOI: 10.1039/C7TC05775J
Citation: J. Mater. Chem. C, 2018, Advance Article
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    Oxidation of rubrene, and implications for device stability

    J. T. Ly, S. A. Lopez, J. B. Lin, J. J. Kim, H. Lee, E. K. Burnett, L. Zhang, A. Aspuru-Guzik, K. N. Houk and A. L. Briseno, J. Mater. Chem. C, 2018, Advance Article , DOI: 10.1039/C7TC05775J

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