Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide

Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide

The new symmetric acyclic -bis(1-pyrenyl) squaramide ( ) functionalized with the pyrene moiety as a fluorogenic fragment has been designed and its ability to selectively detect specific anions and metals investigated. selectively binds Cl both in solution (DMSO 0.5% H O and MeCN) and in the solid st...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2021-02, Vol.26 (5), p.1301
Hauptverfasser: Picci, Giacomo, Milia, Jessica, Aragoni, Maria Carla, Arca, Massimiliano, Coles, Simon J, Garau, Alessandra, Lippolis, Vito, Montis, Riccardo, Orton, James B, Caltagirone, Claudia
Format: Artikel
Sprache:eng
Schlagworte:
Acetonitriles - chemistry
anion recognition
Anions
Anions - chemistry
Coordination Complexes - chemistry
Copper
Copper - chemistry
Copper compounds
Density Functional Theory
DFT
Emissions
Fluorescence
metal sensing
Models, Molecular
Molecular Conformation
Pyrene
Pyrenes - chemistry
Quinine - analogs & derivatives
Quinine - chemistry
Sensors
Spectrometry, Fluorescence
squaramides
supramolecular chemistry
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Zusammenfassung:The new symmetric acyclic -bis(1-pyrenyl) squaramide ( ) functionalized with the pyrene moiety as a fluorogenic fragment has been designed and its ability to selectively detect specific anions and metals investigated. selectively binds Cl both in solution (DMSO 0.5% H O and MeCN) and in the solid state, and allows to selectively detect Cu in MeCN with the formation of a 2:1 metal-receptor complex, with a green intense emission appreciable by naked eye under the UV lamp. The copper complex preserves its emission properties in the presence of Cl . The addition of basic anions (OH , CN , and F ) up to 10 equivalents caused the deprotonation of the squaramide NHs and a dramatic change of the emission properties of the copper complex.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules26051301