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Zn2+/Cd2+ optical discrimination by fluorescent chemosensors based on 8-hydroxyquinoline derivatives and sulfur-containing macrocyclic units

Zn2+/Cd2+ optical discrimination by fluorescent chemosensors based on 8-hydroxyquinoline derivatives and sulfur-containing macrocyclic units
Zn2+/Cd2+ optical discrimination by fluorescent chemosensors based on 8-hydroxyquinoline derivatives and sulfur-containing macrocyclic units
Four new fluorescent chemosensors for metal ions based on 8-hydroxyquinoline (8-HDQ) derivatives and sulfur-containing macrocyclic units were synthesized and characterized, namely 1-(5-chloro-8-hydroxy-7-quinolinylmethyl)-1-aza-4,7,10-trithiacyclododecane (L1), 1-(5-chloro-8-hydroxy-7-quinolinylmethyl)-1-aza-4,13-dithia-7,10-dioxacyclopentadecane (L2), 1-(8-hydroxy-2-quinolinylmethyl)-1-aza-4,7,10-trithiacyclododecane (L3), and 1-(8-hydroxy-2-quinolinylmethyl)-1-aza-4,13-dithia-7,10-dioxacyclopentadecane (L4). Preliminary fluorimetric titrations indicated L1 as the only member of the family of ligands to give a selective CHEF-type response to the presence of Zn2+ in MeCN–H2O (1 : 1, v/v) solutions, which allowed imaging of this metal ion in Cos-7 cells in vitro. The other ligands either did not show any fluorescence response (L3, L4) to any of the metal ions considered (Cu2+, Zn2+, Cd2+, Hg2+ and Pb2+) or gave (L2) a CHEF-type response also to the presence of Cd2+. The coordination properties of L1 towards Zn2+ were, therefore, fully investigated by potentiometric measurements and absorption and emission spectroscopy at different pH values, which indicated that the formation of 2 : 1 L1/Zn2+ complexes is responsible for the CHEF-type effect observed. The complexes [Zn(L1)2H2O](BF4)2 and [Zn(L3)](ClO4)2 were characterized in the solid state by X-ray crystallography, and DFT calculations were performed to understand the origin of the Zn2+/Cd2+ optical discrimination of the 8-HDQ-based “conjugate” fluorescent chemosensors reported.
0300-9246
14516-14530
Aragoni, M. Carla
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Arca, Massimiliano
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Bencini, Andrea
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Caltagirone, Claudia
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Garau, Alessandra
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Isaia, Francesco
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Light, Mark E.
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Lippolis, Vito
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Lodeiro, Carlos
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Mameli, Marta
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Montis, Riccardo
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Mostallino, M. Cristina
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Pintus, Anna
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Puccioni, Stefano
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Aragoni, M. Carla
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Arca, Massimiliano
f90b59f6-4dfb-471d-912e-3515e6507165
Bencini, Andrea
71efef4c-46b3-4f0c-9520-9b001adedb08
Caltagirone, Claudia
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Garau, Alessandra
0dbe375e-901e-4003-9700-45926d87a771
Isaia, Francesco
11f997fe-81a3-4298-bbdc-15e5f2bf18cc
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Lippolis, Vito
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Lodeiro, Carlos
01adab79-eca7-45b2-9143-c74885575464
Mameli, Marta
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Montis, Riccardo
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Mostallino, M. Cristina
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Pintus, Anna
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Puccioni, Stefano
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Aragoni, M. Carla, Arca, Massimiliano, Bencini, Andrea, Caltagirone, Claudia, Garau, Alessandra, Isaia, Francesco, Light, Mark E., Lippolis, Vito, Lodeiro, Carlos, Mameli, Marta, Montis, Riccardo, Mostallino, M. Cristina, Pintus, Anna and Puccioni, Stefano (2013) Zn2+/Cd2+ optical discrimination by fluorescent chemosensors based on 8-hydroxyquinoline derivatives and sulfur-containing macrocyclic units. Dalton Transactions, 42 (40), 14516-14530. (doi:10.1039/c3dt51292d).

Record type: Article

Abstract

Four new fluorescent chemosensors for metal ions based on 8-hydroxyquinoline (8-HDQ) derivatives and sulfur-containing macrocyclic units were synthesized and characterized, namely 1-(5-chloro-8-hydroxy-7-quinolinylmethyl)-1-aza-4,7,10-trithiacyclododecane (L1), 1-(5-chloro-8-hydroxy-7-quinolinylmethyl)-1-aza-4,13-dithia-7,10-dioxacyclopentadecane (L2), 1-(8-hydroxy-2-quinolinylmethyl)-1-aza-4,7,10-trithiacyclododecane (L3), and 1-(8-hydroxy-2-quinolinylmethyl)-1-aza-4,13-dithia-7,10-dioxacyclopentadecane (L4). Preliminary fluorimetric titrations indicated L1 as the only member of the family of ligands to give a selective CHEF-type response to the presence of Zn2+ in MeCN–H2O (1 : 1, v/v) solutions, which allowed imaging of this metal ion in Cos-7 cells in vitro. The other ligands either did not show any fluorescence response (L3, L4) to any of the metal ions considered (Cu2+, Zn2+, Cd2+, Hg2+ and Pb2+) or gave (L2) a CHEF-type response also to the presence of Cd2+. The coordination properties of L1 towards Zn2+ were, therefore, fully investigated by potentiometric measurements and absorption and emission spectroscopy at different pH values, which indicated that the formation of 2 : 1 L1/Zn2+ complexes is responsible for the CHEF-type effect observed. The complexes [Zn(L1)2H2O](BF4)2 and [Zn(L3)](ClO4)2 were characterized in the solid state by X-ray crystallography, and DFT calculations were performed to understand the origin of the Zn2+/Cd2+ optical discrimination of the 8-HDQ-based “conjugate” fluorescent chemosensors reported.

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Accepted/In Press date: 6 August 2013
e-pub ahead of print date: 7 August 2013
Published date: 23 October 2013

Identifiers

Local EPrints ID: 385746
URI: https://eprints.soton.ac.uk/id/eprint/385746
ISSN: 0300-9246
PURE UUID: 071cb02d-c786-4708-a711-af486825226c
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 21 Jan 2016 15:29
Last modified: 17 Jul 2019 01:05

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Contributors

Author: M. Carla Aragoni
Author: Massimiliano Arca
Author: Andrea Bencini
Author: Claudia Caltagirone
Author: Alessandra Garau
Author: Francesco Isaia
Author: Mark E. Light ORCID iD
Author: Vito Lippolis
Author: Carlos Lodeiro
Author: Marta Mameli
Author: Riccardo Montis
Author: M. Cristina Mostallino
Author: Anna Pintus
Author: Stefano Puccioni

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