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 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.
Anion recognition, DFT, Metal sensing, Squaramides, Supramolecular chemistry
Picci, Giacomo
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Milia, Jessica
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Aragoni, M. Carla
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Arca, Massimiliano
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Coles, Simon J.
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Garau, Alessandra
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Lippolis, Vito
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Montis, Riccardo
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Orton, James
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Caltagirone, Claudia
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March 2021
Picci, Giacomo
c95864bc-877f-4cea-a761-276ea5a10c6a
Milia, Jessica
5d0b966b-b102-4b6c-b6c0-59b82d90fe50
Aragoni, M. Carla
3e73ed7a-2cf7-4f5e-9359-61d6e34a6cd5
Arca, Massimiliano
f90b59f6-4dfb-471d-912e-3515e6507165
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Garau, Alessandra
0dbe375e-901e-4003-9700-45926d87a771
Lippolis, Vito
d9833a14-4aab-4827-a2ba-be818871dcf5
Montis, Riccardo
2d2d60eb-b455-414a-80d8-d5a58002bd92
Orton, James
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Caltagirone, Claudia
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Picci, Giacomo, Milia, Jessica, Aragoni, M. Carla, Arca, Massimiliano, Coles, Simon J., Garau, Alessandra, Lippolis, Vito, Montis, Riccardo, Orton, James and Caltagirone, Claudia
(2021)
Switching-on fluorescence by copper (II) and basic anions: A case study with a pyrene-functionalized squaramide.
Molecules, 26 (5), [1301].
(doi:10.3390/molecules26051301).
Abstract
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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Accepted/In Press date: 22 February 2021
Published date: March 2021
Additional Information:
Funding Information:
Funding: Financial support from MIUR (PRIN 2017 project 2017EKCS35) is gratefully acknowledged by C.C., G.P. and V.L., C.C., V.L., M.A., M.C.M. thank Università degli Studi di Cagliari (FIR 2016– 2019), Fondazione di Sardegna (FdS Progetti Biennali di Ateneo, annualità 2018) for financial support.
Publisher Copyright:
Copyright: © 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 (https://creativecommons.org/licenses/by/ 4.0/).
Keywords:
Anion recognition, DFT, Metal sensing, Squaramides, Supramolecular chemistry
Identifiers
Local EPrints ID: 447862
URI: http://eprints.soton.ac.uk/id/eprint/447862
ISSN: 1420-3049
PURE UUID: e8c36d55-6fdd-47e9-81b7-6150e7951bde
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Date deposited: 25 Mar 2021 17:30
Last modified: 17 Mar 2024 02:48
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Contributors
Author:
Giacomo Picci
Author:
Jessica Milia
Author:
M. Carla Aragoni
Author:
Massimiliano Arca
Author:
Alessandra Garau
Author:
Vito Lippolis
Author:
Riccardo Montis
Author:
James Orton
Author:
Claudia Caltagirone
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