Synthesis and Complexation Behavior of 2-[N, N-Bis (1-naphthylmethyl)-aminomethyl]-18-crown-6

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  • Kubo Kanji
    Institute of Advanced Material Study Kyushu University
  • Sakaguchi Seiji
    Department of Applied Chemistry Faculty of Engineering Kanagawa University
  • Sakurai Tadamitsu
    Department of Applied Chemistry Faculty of Engineering Kanagawa University

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  • Synthesis and Complexation Behavior of

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Abstract

2-[N,N-Bis(1-naphthylmethyl)-aminomethyl]-18-crown-6 (3) gave intramolecular exciplex fluorescence, showing that the excited naphthalene chromophore was quenched by the nitrogen atom in the armed crown unit. The armed crown ether (3) was found to display unique photophysical properties in the presence of metal salts. Complexation of 3 with Zn^<2+> increased the fluorescence intensity of the host by a factor of 2.4. ^1H and ^<13>C NMR analyses of this complexation behavior revealed that Zn^<2+> strongly coordinates with the armed crown nitrogen to cause a dramatic decrease in an intramolecular charge-transfer character.

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