Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide
2021
Giacomo Picci | Jessica Milia | Maria Carla Aragoni | Massimiliano Arca | Simon J. Coles | Alessandra Garau | Vito Lippolis | Riccardo Montis | James B. Orton | Claudia Caltagirone
The new symmetric acyclic N,N’-bis(1-pyrenyl) squaramide (H2L) functionalized with the pyrene moiety as a fluorogenic fragment has been designed and its ability to selectively detect specific anions and metals investigated. H2L selectively binds Cl− both in solution (DMSO 0.5% H2O and MeCN) and in the solid state, and allows to selectively detect Cu2+ 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 H2L 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 H2L copper complex.
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