98453-04-4Relevant academic research and scientific papers
Oxidation of rubrene, and implications for device stability
Ly, Jack T.,Lopez, Steven A.,Lin, Janice B.,Kim, Jae Joon,Lee, Hyunbok,Burnett, Edmund K.,Zhang, Lei,Aspuru-Guzik, Alán,Houk,Briseno, Alejandro L.
, p. 3757 - 3761 (2018)
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.
Transformations photochimiques d'endoperoxydes derives d'hydrocarbures aromatiques polycycliques V. Cas de I'endoperoxyde de rubrene: formation d'un nouveau type de photo-isomere
Rigaudy, Jean,Cuong, Nguyen Kim,Godard, Jean-Yves
, p. 78 - 83 (2007/10/02)
Photolysis in benzene at long wavelengths (λ>=420 nm) of rubrene endoperoxide. 11 affords mainly the bicyclic acetal 18, accompanied by the rubrene "iso-oxyde" 22 and by a new isomer: 11b-phenoxy-5a,6,11-triphenyl-5a,11b-dihydro-naphto cyclobutabenzo(b)furan 23, the structure of which has been established by 13C NMR.These various compounds result very likely from subsequent isomerizations of the two unstable meso-diepoxydes 13 and 14 arising first in the process.Moreover, diepoxide 14, precursor of 22 and 23, has been trapped by N-methylmaleimide as adduct 15.
