Tritopic Bis-Urea Receptors for Anion and Ion-Pair Recognition

Jancarlo Gomez-Vega*, Jesús Martín Soto-Cruz, Octavio Juárez-Sánchez, Hisila Santacruz-Ortega, Juan Carlos Gálvez-Ruiz, David Octavio Corona-Martínez, Refugio Pérez-González, Karen Ochoa Lara

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

This work reports on the synthesis and characterization of three tritopic receptors and their binding properties toward various anions, as their tetrabutylammonium salts, and three alkali metal-acetate salts by UV-vis, fluorescence, 1H, 7Li, 23Na, and 39K NMR in MeCN/dimethyl sulfoxide (DMSO) 9:1 (v/v). Molecular recognition studies showed that the receptors have good affinity for oxyanions. Furthermore, these compounds are capable of ion-pair recognition of the alkali metal-acetate salts studied through a cooperative mechanism. Additionally, molecular modeling at the density functional theory (DFT) level of some lithium and sodium acetate complexes illustrates the ion-pair binding capacity of receptors. The anion is recognized through strong hydrogen bonds of the NH- groups from the two urea sites, while the cation interacts with the oxygen atoms of the polyether spacer. This work demonstrates that these compounds are good receptors for anions and ion pairs.

Original languageEnglish
Pages (from-to)22244-22255
Number of pages12
JournalACS Omega
Volume7
Issue number26
DOIs
StatePublished - 5 Jul 2022

Bibliographical note

Funding Information:
This work received financial support from the National Council of Science and Technology of Mexico (CONACyT) in the form of a postgraduate grant for JMSC, and through projects CB-239581 and 281251 (Supramolecular Chemistry Thematic Network). J.G.-V. thanks the University of Sonora for the postdoctoral fellowship. The authors thank Prof. Ivan Castillo-Pérez and Q. María de la Paz Orta-Pérez for assistance with the Elemental Analysis and acknowledge access to “Laboratorios de Servicios Analíticos” of the Institute of Chemistry of the National Autonomous University of Mexico.

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

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