Thiourea-Based Receptors for Anion Recognition and Signaling

Jancarlo Gomez-Vega, Adrian Vasquez-Cornejo, Octavio Juárez-Sánchez, David O. Corona-Martínez, Adrián Ochoa-Terán, Karla A. López-Gastelum, Rogerio R. Sotelo-Mundo, Hisila Santacruz-Ortega, Juan Carlos Gálvez-Ruiz, Refugio Pérez-González, Karen Lillian Ochoa Lara*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

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 1H 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 K1 = 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.

Original languageEnglish
Pages (from-to)4412-4422
Number of pages11
JournalACS Omega
Volume9
Issue number4
DOIs
StatePublished - 30 Jan 2024

Bibliographical note

Publisher Copyright:
© 2024 The Authors. Published by American Chemical Society.

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