Photochemistry of Amino-Linked Bichromophoric Anthracenes. Efficient Cyclomerization of 9-(1-Naphthylmethylaminomethyl)anthracene and Adiabatic Cycloreversion of the Cyclomer

この論文にアクセスする

この論文をさがす

著者

抄録

The spectral and photochemical properties of the title compound <b>1</b> and bis(9-anthrylmethyl)amine (<b>2</b>) have been investigated. The fluorescence spectrum of <b>1</b> in methylcyclohexane showed an emission from the locally excited state of the anthracene part and a weak broad emission at 410—550 nm from the intramolecular exciplex. The fluorescence quantum yields of <b>1</b> and <b>2</b> decreased along with an increase in the solvent polarity. Both <b>1</b> and <b>2</b> underwent intramolecular [4+4] cycloaddition. The quantum yield of the cyclomerization of <b>1</b> was 0.24 in acidic methanol, while in MeCN the reaction was completely quenched by an intramolecular electron transfer from the amino group to the excited anthracene moiety. Excitation of the cyclomer from <b>1</b> at 285 nm brought about fluorescene from both the locally excited anthracene and the exciplex state, indicating that adiabatic cycloreversion took place on the S<sub>1</sub> potential surface. To investigate the conformations, the crystal structures of <b>1</b> and <b>2</b> were determined and PM3 calculations were performed for <b>1</b>–H<sup>+</sup>. The calculations indicate that a conformer in which the two chromophores are located close to each other has a higher energy then other stable conformers.

収録刊行物

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 70(4), 869-875, 1997-04-15

    The Chemical Society of Japan

参考文献:  19件中 1-19件 を表示

  • <no title>

    BOUAS-LAURENT H.

    Pure Appl. Chem. 52, 2633, 1980

    被引用文献4件

  • <no title>

    BECKER H. -D.

    Chem. Rev. 93, 145, 1993

    被引用文献7件

  • <no title>

    BECKER H. -D.

    Advances in Photochemistry 15, 139-227, 1990

    被引用文献2件

  • <no title>

    MORI Y.

    J. Chem. Soc. Perkin Trans. 2 1996, 113

    被引用文献1件

  • <no title>

    CHANDROSS E. A.

    J. Am. Chem. Soc. 95, 611, 1973

    被引用文献1件

  • <no title>

    DESVERGNE J. -P.

    J. Chem. Soc., Perkin Trans. 2 1983, 109

    被引用文献1件

  • <no title>

    FERGUSTON J.

    Mol. Phys. 26, 1457 and 1467, 1974

    被引用文献1件

  • <no title>

    MUROV S. L.

    Handbook of Photochemistry, 1973

    被引用文献16件

  • <no title>

    BECKER H. -D.

    J. Org. Chem. 48, 4542, 1983

    被引用文献1件

  • <no title>

    TAZUKE S.

    Tetrahedron Lett. 23, 197, 1982

    被引用文献3件

  • <no title>

    STEWART J. J. P.

    J. Comput. Chem. 10, 209, 1989

    被引用文献66件

  • <no title>

    ALBINI A.

    J. Am. Chem. Soc. 110, 7760, 1988

    被引用文献2件

  • <no title>

    HARTMANN M.

    Z. Chem. 19, 373, 1979

    被引用文献1件

  • <no title>

    SHELDRICK G. M.

    SHELXS 86, Program for Crystal Structure Determination, 1986

    被引用文献14件

  • <no title>

    TEXSAN: Crystal Structure Analysis Package, 1985

    被引用文献10件

  • <no title>

    STEWART J. J. P.

    MOPAC Ver6.0

    被引用文献2件

  • <no title>

    JOHNSON C. K.

    ORTEP, Report ORNL-3794, 1965

    被引用文献5件

  • <no title>

    HIRAYAMA F.

    J. Chem. Phys. 42, 3163, 1965

    DOI 被引用文献9件

  • <no title>

    BEESON J. C.

    J. Fluorescence 3, 65, 1993

    DOI 被引用文献1件

各種コード

  • NII論文ID(NAID)
    10008917731
  • NII書誌ID(NCID)
    AA00580132
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    00092673
  • NDL 記事登録ID
    4196835
  • NDL 雑誌分類
    ZP1(科学技術--化学・化学工業)
  • NDL 請求記号
    Z53-B35
  • データ提供元
    CJP書誌  NDL  J-STAGE 
ページトップへ