H-bond stabilization of a tautomeric coumarin-pyrazole-pyridine triad generates a PET driven, reversible and reusable fluorescent chemosensor for anion detection

被引:25
作者
Alkis, Meltem [1 ]
Pekyilmaz, Damla [1 ]
Yalcin, Ergin [1 ]
Aydiner, Burcu [1 ]
Dede, Yavuz [1 ]
Seferoglu, Zeynel [1 ]
机构
[1] Gazi Univ, Fac Sci, Dept Chem, Tekn Kullar, TR-06500 Ankara, Turkey
关键词
Coumarin-pyrazolone-pyridine triad; Tautomerism; Anion detection; DFT calculations; PET; ESIPT; FLUORIDE ANION; ON FLUORESCENT; SENSOR; RECOGNITION; LUMINESCENT; SELECTIVITY; HIGHLIGHTS; RECEPTOR; HYBRID; PROBES;
D O I
10.1016/j.dyepig.2017.03.011
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A coumarin based anion sensor utilizing pyrazole both as an electron donor and hydroxyl H-bond donor and pyridine as a tautomer stabilizer is reported. The chemosensor exhibits ON-OFF-ON states and is more sensitive to F- at the stoichiometric ratio of 1:1. The OFF state is due to PET and the role of pyrazole is two fold, both stabilization of the enol tautomer via H-bonding and hosting domain of electrons enabling PET. Moreover, the absorption and emission properties of chemosensor change drastically upon acidification. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:493 / 500
页数:8
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