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

The new symmetric acyclic N,N’-bis(1-pyrenyl) squaramide (H(2)L) functionalized with the pyrene moiety as a fluorogenic fragment has been designed and its ability to selectively detect specific anions and metals investigated. H(2)L selectively binds Cl(−) both in solution (DMSO 0.5% H(2)O and MeCN)...

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Autores principales: Picci, Giacomo, Milia, Jessica, Aragoni, Maria Carla, Arca, Massimiliano, Coles, Simon J., Garau, Alessandra, Lippolis, Vito, Montis, Riccardo, Orton, James B., Caltagirone, Claudia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7957675/
https://www.ncbi.nlm.nih.gov/pubmed/33670937
http://dx.doi.org/10.3390/molecules26051301
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author Picci, Giacomo
Milia, Jessica
Aragoni, Maria Carla
Arca, Massimiliano
Coles, Simon J.
Garau, Alessandra
Lippolis, Vito
Montis, Riccardo
Orton, James B.
Caltagirone, Claudia
author_facet Picci, Giacomo
Milia, Jessica
Aragoni, Maria Carla
Arca, Massimiliano
Coles, Simon J.
Garau, Alessandra
Lippolis, Vito
Montis, Riccardo
Orton, James B.
Caltagirone, Claudia
author_sort Picci, Giacomo
collection PubMed
description The new symmetric acyclic N,N’-bis(1-pyrenyl) squaramide (H(2)L) functionalized with the pyrene moiety as a fluorogenic fragment has been designed and its ability to selectively detect specific anions and metals investigated. H(2)L selectively binds Cl(−) both in solution (DMSO 0.5% H(2)O and MeCN) and in the solid state, and allows to selectively detect Cu(2+) 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 H(2)L 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 H(2)L copper complex.
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spelling pubmed-79576752021-03-16 Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide † Picci, Giacomo Milia, Jessica Aragoni, Maria Carla Arca, Massimiliano Coles, Simon J. Garau, Alessandra Lippolis, Vito Montis, Riccardo Orton, James B. Caltagirone, Claudia Molecules Article The new symmetric acyclic N,N’-bis(1-pyrenyl) squaramide (H(2)L) functionalized with the pyrene moiety as a fluorogenic fragment has been designed and its ability to selectively detect specific anions and metals investigated. H(2)L selectively binds Cl(−) both in solution (DMSO 0.5% H(2)O and MeCN) and in the solid state, and allows to selectively detect Cu(2+) 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 H(2)L 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 H(2)L copper complex. MDPI 2021-02-28 /pmc/articles/PMC7957675/ /pubmed/33670937 http://dx.doi.org/10.3390/molecules26051301 Text en © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Picci, Giacomo
Milia, Jessica
Aragoni, Maria Carla
Arca, Massimiliano
Coles, Simon J.
Garau, Alessandra
Lippolis, Vito
Montis, Riccardo
Orton, James B.
Caltagirone, Claudia
Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide †
title Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide †
title_full Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide †
title_fullStr Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide †
title_full_unstemmed Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide †
title_short Switching-On Fluorescence by Copper (II) and Basic Anions: A Case Study with a Pyrene-Functionalized Squaramide †
title_sort switching-on fluorescence by copper (ii) and basic anions: a case study with a pyrene-functionalized squaramide †
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7957675/
https://www.ncbi.nlm.nih.gov/pubmed/33670937
http://dx.doi.org/10.3390/molecules26051301
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