Design and Function of Novel Azoprobe Possessing Multipoint Binding Sites for Dopamine Recognition

水中でドーパミンに対し選択的に応答するプローブを開発することを目的として，クラウンエーテル及びボロン酸基を持つアゾプローブ1 {2-[3,4-(18-crown-6)phenylazo]-5-hydroxy-phenylboronic acid}を設計した．1は水に溶け，pHの増加に伴い黄色→赤色→橙色へと色変化した．また，ドーパミン及び類似化合物添加時の紫外─可視吸収スペクトルより，プローブとゲスト分子が1 : 1型の複合体を形成すると仮定して結合定数の算出を行ったところ，結合定数はドーパミンで最も高い値（1.11±0.021）×102 M−1が得られ，pH 8でドーパミンを添加すると赤色から橙色へ色変化した．この変化はフェノール水酸基のプロトン解離によるものであると示唆された．種々のゲスト分子との応答挙動から，本プローブは1,2-シスジオール部位を持つゲスト分子に大きく影響を受けることを明らかにした．

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