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Naji, M. |
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Motta, Antonella |
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Aletan, Dirar |
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Mohamed, Tarek |
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Ertürk, Emre |
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Taccardi, Nicola |
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Kononenko, Denys |
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Petrov, R. H. | Madrid |
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Alshaaer, Mazen | Brussels |
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Bih, L. |
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Casati, R. |
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Muller, Hermance |
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Kočí, Jan | Prague |
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Šuljagić, Marija |
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Kalteremidou, Kalliopi-Artemi | Brussels |
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Azam, Siraj |
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Ospanova, Alyiya |
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Blanpain, Bart |
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Ali, M. A. |
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Popa, V. |
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Rančić, M. |
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Ollier, Nadège |
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Azevedo, Nuno Monteiro |
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Landes, Michael |
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Rignanese, Gian-Marco |
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Liñares, Araceli
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article
Novel trans-disubstituted hexaaza-macrocyclic ligands containing pyridine head units: Synthesis, disubstitution and colorimetric properties
Abstract
<p>A trans-N,N′-methylated hexaazamacrocycle precursor L<sup>3</sup>, derived from the hexadentate polyamine macrocycle L (Py2[18]aneN6), was synthesized for the first time. The crystal structures of the intermediates L<sup>1</sup>·8H<sub>2</sub>O and L<sup>2</sup>I<sub>2</sub>·H<sub>2</sub>O showing two trans quaternary nitrogen atoms have also been determined by single-crystal X-ray crystallography. By the alkylation of the trans secondary amines present in L<sup>3</sup>, two novel macrocyclic molecular probes 1 and 2 linked to two nitrophenylurea and two nitrophenylthiourea groups, respectively, are reported. Crystals of 1·2CDCl<sub>3</sub> suitable for single-crystal X-ray diffraction analysis were also obtained. The coordination ability of compounds 1 and 2 toward hydrated nitrate salts of cobalt(II), nickel(II), copper(II), zinc(II) and cadmium(II) was studied. Their responses toward different anions (fluoride (F<sup>-</sup>), chloride (Cl<sup>-</sup>), bromide (Br<sup>-</sup>), iodide (I<sup>-</sup>), hydroxide (OH<sup>-</sup>), acetate (AcO<sup>-</sup>), cyanide (CN<sup>-</sup>), dihydrogen phosphate (H<sub>2</sub>PO<sub>4</sub><sup>-</sup>), nitrate (NO<sub>3</sub><sup>-</sup>) and perchlorate (ClO<sub>4</sub><sup>-</sup>)) in DMSO solution were evaluated by UV-vis absorption spectroscopy. The immobilization of probe 1 in cellulose supported systems to evaluate its efficiency in the fast recognition of different anions (F<sup>-</sup>, AcO<sup>-</sup>, CN<sup>-</sup>, H<sub>2</sub>PO<sub>4</sub><sup>-</sup>) in aqueous phase was also described.</p>