Fluorescent “Turn-Off” Detection of Fluoride and Cyanide Ions Using Zwitterionic Spirocyclic Meisenheimer Compounds

Stable zwitterionic spirocyclic Meisenheimer compounds were synthesized using a one-step reaction between picric acid and diisopropyl (ZW1) or dicyclohexyl (ZW3) carbodiimide. A solution of these compounds displays intense orange fluorescence upon UV or visible light excitation, which can be quenche...

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Bibliographic Details
Main Authors: Marina Benet, Marc Villabona, Carles Llavina, Silvia Mena, Jordi Hernando, Rabih O. Al-Kaysi, Gonzalo Guirado
Format: Article
Language:English
Published: MDPI AG 2017-10-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/22/11/1842
Description
Summary:Stable zwitterionic spirocyclic Meisenheimer compounds were synthesized using a one-step reaction between picric acid and diisopropyl (ZW1) or dicyclohexyl (ZW3) carbodiimide. A solution of these compounds displays intense orange fluorescence upon UV or visible light excitation, which can be quenched or “turned-off” by adding a mole equivalent amount of F− or CN− ions in acetonitrile. Fluorescence is not quenched in the presence of other ions such as Cl−, Br−, I−, NO2−, NO3−, or H2PO4−. These compounds can therefore be utilized as practical colorimetric and fluorescent probes for monitoring the presence of F− or CN− anions.
ISSN:1420-3049