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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)...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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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. |
format | Online Article Text |
id | pubmed-7957675 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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