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Molecules 2017, 22(11), 1842; doi:10.3390/molecules22111842

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

1
Departament de Química, Universitat Autònoma de Barcelona, E-08193 Bellaterra, 08193 Barcelona, Spain
2
College of Science and Health Professions-3124, King Saud bin Abdulaziz University for Health Sciences/King Abdullah International Medical Research Center, Ministry of National Guard Health Affairs, 11426 Riyadh, Saudi Arabia
*
Authors to whom correspondence should be addressed.
Received: 27 September 2017 / Revised: 25 October 2017 / Accepted: 26 October 2017 / Published: 27 October 2017
(This article belongs to the Special Issue Advances in Spiro Compounds)
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Abstract

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. View Full-Text
Keywords: spirocyclic; Meisenheimer complex; fluoride; cyanide; colorimetric; fluorescence; zwitterionic spirocyclic; Meisenheimer complex; fluoride; cyanide; colorimetric; fluorescence; zwitterionic
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MDPI and ACS Style

Benet, M.; Villabona, M.; Llavina, C.; Mena, S.; Hernando, J.; Al-Kaysi, R.O.; Guirado, G. Fluorescent “Turn-Off” Detection of Fluoride and Cyanide Ions Using Zwitterionic Spirocyclic Meisenheimer Compounds. Molecules 2017, 22, 1842.

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