The One-Electron Transfer Induced Photocycloreversion of Stilbazolium Cyclodimers

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Abstract

The irradiation of iodide salts of stereo isomeric stilbazolium cyclodimers in their CT bands (ca. 355 nm) resulted in a one-electron transfer induced photocycloreversion, which led to the formation of stilbazolium ions; the quantum yields (<i>Φ</i>) being highly sensitive to their structures, i.e., the <i>Φ</i> for <i>syn</i>-Head-to-Head (<i>syn</i>-HH) was found to be 0.35, for <i>syn</i>-Head-to-Tail (<i>syn</i>-HT) 0.0026, and for <i>anti</i>-Head-to-Head (<i>anti</i>-HH) 0.00095, respectively. This reaction shows a distinct contrast to photocycloreversion by irradiation at 255 nm, which resulted in a highly efficient, but nonselective, splitting, the <i>Φ</i>’s being in the range of 0.3—0.8. In the photosensitized cycloreversion of methyl sulfate salts of dimers using 9,10-dimethoxyanthracene (DMA) as a sensitizer, the quantum efficiencies show a structural dependence similar to the above case of irradiation at their CT bands. Cosensitization with DMA and 1-cyanonaphthalene as an electron mediator resulted in relative quantum yields showing a close coincidence to the yields in the irradiation of the CT band, i.e., 254 : 2.6 : 1 for <i>syn</i>-HH, <i>syn</i>-HT, and <i>anti</i>-HH, respectively. This implies that the one-electron transfer mechanism can be initiated both by CT band irradiation as well as DMA sensitization. It can be concluded that the structural dependence of the quantum efficiencies is attributed to the through-bond interaction of two pyridinium rings, which facilitates the splitting of the C–C bond in the cyclobutane ring.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 71(2), 419-424, 1998-02-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008928789
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4406062
  • NDL Source Classification
    ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-B35
  • Data Source
    CJP  NDL  J-STAGE 
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