Coumarin–Spiropyran Dyad with a Hydrogenated Pyran Moiety for Rapid, Selective, and Sensitive Fluorometric Detection of Cyanide Anion

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• 作者：Yasuhiro Shiraishi ; Masaya Nakamura ; Naoto Hayashi ; Takayuki Hirai
• 刊名：Analytical Chemistry
• 出版年：2016
• 出版时间：July 5, 2016
• 年：2016
• 卷：88
• 期：13
• 页码：6805-6811
• 全文大小：478K
• 年卷期：0
• ISSN：1520-6882

文摘

We synthesized a coumarin–spiropyran dyad with a hydrogenated pyran moiety (2), behaving as an off–on type fluorescent receptor for rapid, selective, and sensitive detection of cyanide anion (CN^–) in aqueous media. The receptor itself shows almost no fluorescence with a quantum yield < 0.01, due to the delocalization of π-electrons over the molecule. Selective nucleophilic addition of CN^– to the spirocarbon of the molecule rapidly promotes spirocycle opening within only 3 min. This leads to localization of π-electrons on the coumarin moiety and exhibits strong light-blue fluorescence at 459 nm with very high quantum yield (0.52). As a result of this, the receptor facilitates rapid, selective, and sensitive fluorometric detection of CN^– as low as 1.0 μM.