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Thiourea-Based Receptors for Anion Recognition and Signaling.

Jancarlo Gomez-VegaAdrian Vasquez-CornejoOctavio Juárez-SánchezDavid O Corona-MartínezAdrián Ochoa-TeránKarla-Alejandra López-GastélumRogerio R Sotelo-MundoHisila Del Carmen Santacruz-OrtegaJuan Carlos Gálvez-RuizRefugio Pérez-GonzálezKaren Ochoa Lara
Published in: ACS omega (2024)
This work reports on two thiourea-based receptors with pyridine and amine units including 1-naphthyl ( MT1N ) and 4-nytrophenyl ( MT4N ) as signaling units. For both compounds, their affinity and signaling ability toward various anions of different geometry and basicity in DMSO were studied using UV-vis, fluorescence, and 1 H NMR techniques. Anion recognition studies revealed that both MT1N and MT4N have, in general, high affinities toward basic anions. In this regard, a higher acidity of the MT4N receptor was demonstrated. Furthermore, MT4N has a higher affinity for fluoride (log K 1 = 5.98) than for the other anions and can effectively detect it through colorimetric changes that can be monitored by the UV-vis technique. The interaction between receptors and anions mainly involves the hydrogens of the amino and thiourea groups of the former. Complementary single-crystal X-ray diffraction studies and molecular modeling at the DFT level were also performed.
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