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Issue 14, 2018
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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 via1H 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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Supplementary files

Article information


Submitted
15 Dec 2017
Accepted
12 Jan 2018
First published
15 Jan 2018

J. Mater. Chem. C, 2018,6, 3757-3761
Article type
Paper

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, 6, 3757
DOI: 10.1039/C7TC05775J

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