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

被引：74

作者：

Shiraishi, Yasuhiro ^{[1
,2
,3
]}

Nakamura, Masaya ^{[1
,2
]}

Hayashi, Naoto ^{[1
,2
]}

Hirai, Takayuki ^{[1
,2
]}

机构：

[1] Osaka Univ, Grad Sch Engn Sci, Res Ctr Solar Energy Chem, Toyonaka, Osaka 5608531, Japan

[2] Osaka Univ, Grad Sch Engn Sci, Div Chem Engn, Toyonaka, Osaka 5608531, Japan

[3] JST, PRESTO, Kawaguchi, Saitama 3320012, Japan

来源：

ANALYTICAL CHEMISTRY | 2016年 / 88卷 / 13期

基金：

日本科学技术振兴机构;

关键词：

FLUORESCENT SENSOR; MICHAEL ACCEPTOR; AQUEOUS-SOLUTION; RECEPTOR; PROBE; WATER; IONS; TRANSFORMATION; CHEMOSENSOR; MOLECULES;

D O I：

10.1021/acs.analchem.6b01279

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

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 pi-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 pi-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 mu M.

引用

页码：6805 / 6811

页数：7

共 54 条

[1] Sensing and discrimination of cyanide and hydrogen sulfide using an 8-alkenyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene derivative [J].