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    Mechanistic studies on the photodegradation of 2,5-dialkyloxyl-substituted para-phenylenevinylene oligomers by singlet oxygen.

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    Authors
    Burrows, Hugh D
    Narwark, Oliver
    Peetz, Ralf
    Thorn-Csányi, Emma
    Monkman, Andrew P
    Hamblett, Ian
    Navaratnam, Suppiah
    Affiliation
    Departamento de Química, Universidade de Coimbra, 304-535, Coimbra, Portugal. burrows@ci.uc.pt
    Issue Date
    2010-07-30
    
    Metadata
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    Abstract
    Time-dependent UV/visible absorption changes are observed on photolysis of aerated solutions of monodisperse, vinyl end-capped 2,5-diheptyloxyl substituted PV-oligomers (OPV, n = 1, 2, 3). In all cases, photolysis occurs in at least two distinct stages. Evidence for the intermediacy of singlet oxygen comes from pulse radiolysis and time-resolved luminescence studies, which confirm formation of the OPV triplet state and its quenching by molecular oxygen to produce singlet oxygen. The subsequent reaction with oligomers is observed directly by time-resolved phosphorescence and indirectly through product identification. The results strongly suggest that the reaction between singlet oxygen and OPV proceeds via cycloaddition, leading to bond scission and aldehyde group formation. The reactivity of vinylene linkages is greater than of vinyl end groups. Consequently, the photostability decreases as the chain length is extended. Implications on the oxidative degradation of poly(p-phenylenevinylene)s in optoelectronic devices, and of competing singlet oxygen and superoxide radical anion degradation pathways, are discussed.
    Citation
    Mechanistic studies on the photodegradation of 2,5-dialkyloxyl-substituted para-phenylenevinylene oligomers by singlet oxygen. 2010, 9 (7):942-8 Photochem. Photobiol Sci
    Journal
    Photochemical & Photobiological Sciences
    URI
    http://hdl.handle.net/10541/111355
    DOI
    10.1039/c0pp00053a
    PubMed ID
    20473426
    Type
    Article
    Language
    en
    ISSN
    1474-9092
    EISSN
    1474-905X
    ae974a485f413a2113503eed53cd6c53
    10.1039/c0pp00053a
    Scopus Count
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    All Paterson Institute for Cancer Research

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