Photolyses of Derivatives of Naphthyl and Anthryl Phosphates and Methylphosphonates

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  • Mitsunobu Nakamura
    The Institute of Scientific and Industrial Research, Osaka UniversityMihogaoka 8-1, Ibaraki, Osaka 567
  • Koichi Sawasaki
    The Institute of Scientific and Industrial Research, Osaka UniversityMihogaoka 8-1, Ibaraki, Osaka 567
  • Yoshiki Okamoto
    The Institute of Scientific and Industrial Research, Osaka UniversityMihogaoka 8-1, Ibaraki, Osaka 567
  • Setsuo Takamuku
    The Institute of Scientific and Industrial Research, Osaka UniversityMihogaoka 8-1, Ibaraki, Osaka 567

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<jats:title>Abstract</jats:title> <jats:p>Upon UV irradiation in acetonitrile, tri-1-naphthyl phosphate and di-1-naphthyl methylphosphonate underwent intramolecular rearrangement and ipso-coupling to give 1,2′-binaphthalen-1′-ol and 1,1′-binaphthalene, respectively. In the photolyses of tris(4-methoxy-1-naphthyl) phosphate and bis(4-methoxy-1-naphthyl) methylphosphonate in methanol, 4,4′-dimethoxy-1,1′ -binaphthalene, 1′,4,4′-trimethoxy-1,2′-binaphthalene, and 2,4,4′-trimethoxy-1,1′-binaphthalene were generated. Tri-9-anthryl phosphate and di-9-anthryl methylphosphonate underwent intramolecular (4+4) photocycloaddition between two anthryl groups. The fluorescence spectra of the naphthyl derivatives had two emission bands ascribed to an intramolecular excimer and a monomer, but the fluorescence spectra of the anthryl derivatives had only a monomer emission band. These photoluminescence behaviors are closely related to the reactivities of the compounds.</jats:p>

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