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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
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
1420-3049
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
4e2a471f-9e11-4cb4-abb6-d0398047939f
Caltagirone, Claudia
9148afed-6af0-4fcd-b30e-daa3d7765dc0
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
4e2a471f-9e11-4cb4-abb6-d0398047939f
Caltagirone, Claudia
9148afed-6af0-4fcd-b30e-daa3d7765dc0

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).

Record type: Article

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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More information

Accepted/In Press date: 22 February 2021
Published date: 28 February 2021
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
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 25 Mar 2021 17:30
Last modified: 26 Mar 2021 02:37

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Contributors

Author: Giacomo Picci
Author: Jessica Milia
Author: M. Carla Aragoni
Author: Massimiliano Arca
Author: Simon J. Coles ORCID iD
Author: Alessandra Garau
Author: Vito Lippolis
Author: Riccardo Montis
Author: James Orton
Author: Claudia Caltagirone

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