Steven A.
Lopez, 
bc
Janice B.
Lin,
b
Hyunbok
Lee,
a
Lei
Zhang,
*ad
K. N.
Houk
*b
and
Alejandro L.
Briseno
*a
bc
Janice B.
Lin,
b
Hyunbok
Lee,
a
Lei
Zhang,
*ad
K. N.
Houk
*b
and
Alejandro L.
Briseno
*a
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.
- This article is part of the themed collection: Celebrating 50 years of Professor Fred Wudl’s contributions to the field of organic semiconductors
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