Fluorescent "turn-Off" detection of fluoride and cyanide ions using zwitterionic spirocyclic meisenheimer compounds

Marina Benet; Marc Villabona; Carles Llavina; Silvia Mena; Jordi Hernando; Rabih O. Al-Kaysi; Gonzalo Guirado

doi:10.3390/molecules22111842

Fluorescent "turn-Off" detection of fluoride and cyanide ions using zwitterionic spirocyclic meisenheimer compounds

Marina Benet, Marc Villabona, Carles Llavina, Silvia Mena, Jordi Hernando, Rabih O. Al-Kaysi, Gonzalo Guirado

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© 2017 by the authors. 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.

Idioma original	Inglés
Número de artículo	1842
Publicación	Molecules
Volumen	22
N.º	11
DOI	https://doi.org/10.3390/molecules22111842
Estado	Publicada - 1 nov 2017

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@article{e64f023a096d4c4b87d5495a0fb202f3,

title = "Fluorescent {"}turn-Off{"} detection of fluoride and cyanide ions using zwitterionic spirocyclic meisenheimer compounds",

abstract = "{\textcopyright} 2017 by the authors. 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.",

keywords = "Colorimetric, Cyanide, Fluorescence, Fluoride, Meisenheimer complex, Spirocyclic, Zwitterionic",

author = "Marina Benet and Marc Villabona and Carles Llavina and Silvia Mena and Jordi Hernando and Al-Kaysi, {Rabih O.} and Gonzalo Guirado",

year = "2017",

month = nov,

day = "1",

doi = "10.3390/molecules22111842",

language = "English",

volume = "22",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "11",

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TY - JOUR

T1 - Fluorescent "turn-Off" detection of fluoride and cyanide ions using zwitterionic spirocyclic meisenheimer compounds

AU - Benet, Marina

AU - Villabona, Marc

AU - Llavina, Carles

AU - Mena, Silvia

AU - Hernando, Jordi

AU - Al-Kaysi, Rabih O.

AU - Guirado, Gonzalo

PY - 2017/11/1

Y1 - 2017/11/1

N2 - © 2017 by the authors. 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.

AB - © 2017 by the authors. 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.

KW - Colorimetric

KW - Cyanide

KW - Fluorescence

KW - Fluoride

KW - Meisenheimer complex

KW - Spirocyclic

KW - Zwitterionic

U2 - 10.3390/molecules22111842

DO - 10.3390/molecules22111842

M3 - Article

SN - 1420-3049

VL - 22

JO - Molecules

JF - Molecules

IS - 11

M1 - 1842

ER -

Fluorescent "turn-Off" detection of fluoride and cyanide ions using zwitterionic spirocyclic meisenheimer compounds

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