Fluorescent Sensors for Molecules. Guest-Responsive Monomer and Excimer Fluorescence of 6A,6B-; 6A,6C- ; 6A,6D- ; and 6A,6E-Bis(2-naphthylsulfonyl)- γ-cyclodextrins

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Flexible hosts, 6A,6B-; 6A,6C-; 6A,6D-; and 6A,6E-bis(2-naphthylsulfonyl)-<i>γ</i>-cyclodextrins (<i>γ</i>-<b>1</b>, <i>γ</i>-<b>2</b>, <i>γ</i>-<b>3</b>, and <i>γ</i>-<b>4</b>, respectively) were used as fluorescent sensors with which a variety of organic compounds were detected by naphthalene excimer and monomer emissions. In a 10 vol% ethylene glycol aqueous solution, <i>γ</i>-<b>1</b> exhibits almost pure monomer fluorescence while <i>γ</i>-<b>2</b>, <i>γ</i>-<b>3</b>, and <i>γ</i>-<b>4</b> exhibit both monomer and excimer emissions. The intensities of the emissions changed upon addition of guest species, particularly in the case of <i>γ</i>-<b>2</b> and <i>γ</i>-<b>3</b>, and the guest-induced intensity variations were used as sensitivity factors of the sensors. When (−)-borneol (<b>5</b>), cyclohexanol (<b>6</b>), cyclododecanol (<b>7</b>), and 1-adamantanecarboxylic acid (<b>8</b>) were added to each host solution, <i>γ</i>-<b>2</b>, <i>γ</i>-<b>3</b>, and <i>γ</i>-<b>4</b> increased the excimer emission intensity but decreased the monomer one, the absolute intensity variations being <b>6</b> < <b>5</b> ≈ <b>8</b> < <b>7</b>. When geraniol (<b>9</b>), nerol (<b>10</b>), and (−)-menthol (<b>11</b>) were added, the hosts decreased intensities in both monomer and excimer emissions for <b>9</b> and <b>10</b> while their emission variations for <b>11</b> were similar to those of <b>5</b>. For steroids such as cholic acid (<b>12</b>), deoxycholic acid (<b>13</b>), chenodeoxycholic acid (<b>14</b>), and ursodeoxycholic acid (<b>15</b>), <i>γ</i>-<b>4</b> showed depression in the excimer emission and enhancement in the monomer one while <i>γ</i>-<b>2</b> and <i>γ</i>-<b>3</b> showed complicated features in which the excimer emission was enhanced with the order of <b>15</b> < <b>14</b> < <b>13</b> ≈ <b>12</b> but the monomer one was depressed or enhanced depending on the hosts. All these data demonstrate that the hosts can be used as sensors for molecular recognition.

収録刊行物

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 70(6), 1339-1346, 1997-06-15

    The Chemical Society of Japan

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各種コード

  • NII論文ID(NAID)
    10008919626
  • 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
    4240140
  • 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 
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