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Fluorescence Turn On of Coumarin Derivatives by Metal Cations: A New Signaling Mechanism Based on C=N Isomerization

Organic Letters · 2006 · Vol. 9(1) · pp. 33–36

Jiasheng Wu✉(City University of Hong Kong)Weimin Liu(Chinese Academy of Sciences)Xiaoqing Zhuang(City University of Hong Kong)Fang Wang(Technical Institute of Physics and Chemistry)Pengfei Wang(Technical Institute of Physics and Chemistry)Silu Tao(Technical Institute of Physics and Chemistry)Xiaohong Zhang(Technical Institute of Physics and Chemistry)Shikang Wu(Chinese Academy of Sciences)Shuit‐Tong Lee(Chinese Academy of Sciences)

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Abstract

[reaction: see text] A new sensing mechanism based on C=N isomerization, which shows a very significant fluorescence enhancement to the metal cations in a simple and efficient way, is demonstrated. A coumarin derivative (L) containing a C=N group was designed as an example for illustration. The free ligand L is almost nonfluorescent due to the isomerization of C=N double bond in the excited state. However, the solution of ligand shows about a 200-fold increase of fluorescence quantum yield (about 30%) upon addition of Zn(ClO4)2.

Molecular Sensors and Ion Detection Luminescence and Fluorescent Materials Advanced biosensing and bioanalysis techniquesIsomerizationChemistryCoumarinFluorescenceQuantum yieldLigand (biochemistry)PhotochemistryTurn (biochemistry)Derivative (finance)Excited state

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