32287-37-9Relevant academic research and scientific papers
Photooxidation of the Evaporated Films of Polycyclic Aromatic Hydrocarbons Studied by X-Ray Photoelectron Spectroscopy
Yamada, Masamichi,Ikemoto, Isao,Kuroda, Haruo
, p. 1057 - 1062 (1988)
Photooxidations of the evaporated films of rubrene, naphthacene, and pentacene were investigated by means of X-ray photoelectron spectroscopy.A rubrene film was found to be photooxidized far more easily than a naphthacene film although the molecules of ru
Direct Near Infrared Light–Activatable Phthalocyanine Catalysts
Katsurayama, Yoshino,Ikabata, Yasuhiro,Maeda, Hajime,Segi, Masahito,Nakai, Hiromi,Furuyama, Taniyuki
, (2021/12/22)
The high penetration of near-infrared (NIR) light makes it effective for use in selective reactions under light-shielded conditions, such as in sealed reactors and deep tissues. Herein, we report the development of phthalocyanine catalysts directly activa
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.
supporting information, p. 3757 - 3761 (2018/04/12)
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.
Connecting molecule oxidation to single crystal structural and charge transport properties in rubrene derivatives
Uttiya,Miozzo,Fumagalli,Bergantin,Ruffo,Parravicini,Papagni,Moret,Sassella
, p. 4147 - 4155 (2014/06/09)
The study of a series of rubrene derivatives appropriately designed for limiting oxidation can be a powerful tool for clarifying the role of oxidation in the transport properties of crystalline rubrene, which is still unclear. Here, the synthesis of a ser
Acene-doped polymer films: Singlet oxygen dosimetry and protein sensing
Koylu, Damla,Sarrafpour, Syena,Zhang, Jingjing,Ramjattan, Sanya,Panzer, Matthew J.,Thomas, Samuel W.
supporting information, p. 9489 - 9491 (2012/11/06)
This paper describes thin films comprising acenes dispersed in a conjugated polymeric host that have a ratiometric photoluminescence response to singlet oxygen. These films also respond to irradiation of protein-bound sensitizers, which represents a solut
Reversible photooxygenation of alkynylanthracenes: Chemical generation of singlet oxygen under very mild conditions
Fudickar, Werner,Linker, Torsten
supporting information; experimental part, p. 13661 - 13664 (2012/01/06)
In the dark and very fast: The generation of singlet oxygen ( 1O2) from endoperoxides, which are readily available by photooxygenation of the corresponding anthracenes, proceeds within minutes in the dark (see scheme), a rate hitherto unknown for other anthracenes or naphthalenes. This provides an efficient chemical source of singlet oxygen under very mild conditions.
Oxidation in three-liquid-phase microemulsion systems using "balanced catalytic surfactants"
Nardello-Rataj, Veronique,Caron, Laurent,Borde, Cedric,Aubry, Jean-Marie
supporting information; experimental part, p. 14914 - 14915 (2009/03/12)
A series of "Balanced Catalytic Surfactants" (BCS) [(Cn)2N(C1)2]2MoO4 (n = 8, 9, 10, 12) based on amphiphilic double-tailed quaternary ammonium with molybdate as a counterion has been developed for the dark singlet [4 + 2] cyclooxygenation of organic substrates in three-liquid-phase microemulsion systems. These cationic surfactants form three-liquid-phase microemulsion systems at room temperature in the presence of an appropriate organic solvent and water without addition of any cosurfactant or electrolyte. Comparative peroxidation of rubrene points out the specific advantages of these three-phase media over phase transfer catalysis in two phase systems and on conventional one-phase microemulsions based on sodium molybdate: (i) only three constituents, (ii) low amounts of surfactants, (iii) insensitivity to water dilution, (iv) fast separation of the three phases, (v) straightforward recovery of the product and the surfactant from the oil and microemulsion phases, respectively. The preparative peroxidation of α-terpinene and 1,4,5-trimethylnaphtalene was performed in the ternary systems [(C8)2N(C1)2]2MoO4/water/tert-butyl acetate or benzene. The reusability of the catalyst, the catalytic nature of the BCS, and the ability of the systems to oxidize poorly reactive substrates were demonstrated showing the broadness of the applicability of such systems. Copyright
Kinetics of the oxygenation of unsaturated organics with singlet oxygen generated from H2O2 by a heterogeneous molybdenum catalyst
Sels, Bert F.,De Vos, Dirk E.,Jacobs, Pierre A.
, p. 6916 - 6926 (2008/02/09)
A heterogeneous catalyst containing MoO42- exchanged on layered double hydroxides (Mo-LDHs) is used to produce 1O 2 from H2O2, and with this dark 1O2, unsaturated hydrocarbons are oxidized in allylic peroxides. The oxidation kinetics are studied in detail and are compared with the kinetics of oxidation by 1O2, formed from H 2O2 by a homogeneous catalyst. A model is proposed for the heterogeneously catalyzed 1O2 generation and peroxide formation. The model divides the reaction suspension in two compartments: (1) the intralamellar and intragranular zones of the LDH catalyst; (2) the bulk solution. The 2-compartment model correctly predicts the oxidant efficiency and peroxide yield for a series of olefin peroxidation reactions. 1O 2 is generated at a high rate by the heterogeneous catalyst, but somewhat more 1O2 is lost by quenching with the heterogeneous catalyst than using the homogeneous catalyst. Quenching occurs mainly as a result of collision with the LDH hydroxyl surface, as is evidenced by using LDH supports containing strong 1O2 deactivators such as Ni2+. A total of 15 organic substrates were peroxidized on a preparative scale using the best Mo-LDH catalyst under optimal conditions.
Calcium peroxide diperoxohydrate as a storable chemical generator of singlet oxygen for organic synthesis
Pierlot, Christel,Nardello, Veronique,Schrive, Jordane,Mabille, Caroline,Barbillat, Jacques,Sombret, Bernard,Aubry, Jean-Marie
, p. 2418 - 2423 (2007/10/03)
Calcium peroxide diperoxohydrate (CaO2·2H2O2) is an environmentally friendly generator of singlet oxygen (1O2, 1Δg) that can be used in organic synthesis as an alternative to the regular photochemical method. This compound produces 1O2 in various solvents and can be easily recovered by filtration for further regeneration. Both monitoring of 1O2 luminescence at 1270 nm and specific trapping have shown that CaO2·2H2O2 can be stored for several days at -80 °C and that the yield of 1O2 is equal to 25%. Oxidation of typical organic substrates in methanol or THF through [4 + 2] or [2 + 2] cycloaddition and ene reaction have been carried out on a preparative scale with total conversion and selectivity.
Preparative oxidation of organic compounds in microemulsions with singlet oxygen generated chemically by the sodium molybdate/hydrogen peroxide system
Aubry, Jean-Marie,Bouttemy, Sabine
, p. 5286 - 5294 (2007/10/03)
A reverse (water in oil) microemulsion has been designed to oxidize hydrophobic organic substrates with singlet oxygen (1O2, 1Δ(g)) generated from the disproportionation of hydrogen peroxide catalyzed by molybdate ions. The microemulsion was prepared by mixing methylene chloride, sodium dodecylsulfate, n-butanol, and aqueous molybdate. Flash photolysis studies have shown that in such media singlet oxygen exhibits a similar kinetic behavior that under homogeneous conditions (τ(Δ) ? 42 μs). Various typical organic substrates have been oxidized on the preparative scale with this chemically generated singlet oxygen, and the expected oxidation products have been isolated in high yields.
