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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Detalhes bibliográficos
Autores: Benet, Marina, Villabona, Marc|||0000-0001-9106-5405, Llavina, Carles, Mena Fernández, Silvia|||0000-0002-2800-2388, Hernando, Jordi|||0000-0002-1126-4138, Al-Kaysi, Rabih O.|||0000-0001-8429-2802, Guirado, Gonzalo|||0000-0003-2128-7007
Formato: artículo
Fecha de publicación:2017
País:España
Recursos:Universitat Autònoma de Barcelona
Repositorio:Dipòsit Digital de Documents de la UAB
Idioma:inglés
OAI Identifier:oai:ddd.uab.cat:201594
Acesso em linha:https://ddd.uab.cat/record/201594
https://dx.doi.org/urn:doi:10.3390/molecules22111842
Access Level:acceso abierto
Palavra-chave:Colorimetric
Cyanide
Fluorescence
Fluoride
Meisenheimer complex
Spirocyclic
Zwitterionic
Descrição
Resumo: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.