Anion, cation and ion-pair recognition by bis-urea based receptors containing a polyether bridge

Jancarlo Gómez-Vega, Ramón Alfonso Moreno-Corral, Hisila Santacruz Ortega, David Octavio Corona-Martínez, Herbert Höpfl, Rogerio R. Sotelo-Mundo, Adrián Ochoa-Terán, Raymundo Enrique Escobar-Picos, José Zeferino Ramírez-Ramírez, Octavio Juárez-Sánchez, Karen Ochoa Lara*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Two bis-urea type receptors were synthesized containing a polyether bridge and two 4-nitrophenyl groups as chromogenic units, R1 and R2. Molecular recognition studies of receptors towards different tetraalkylammonium and alkali metal salts were carried out in DMSO by UV-Vis and 1 H-NMR spectroscopy. The receptors were found to have high affinity for diverse anions and ion-pairs, showing the highest affinities towards the tetramethylammonium and sodium salts. The cation binding ability of the receptors was evidenced by means 1 H NMR, mass spectrometric ESI + studies and the crystal structures of some precursors. Additionally, the molecular modelling at the DFT level of the tetramethylammonium acetate complexes illustrates the potential ion-pair binding ability of the receptors: the anion is recognized through strong hydrogen bonds from the NH─ groups from the two urea sites, while the cation is bound by a combination of cation─π, C-H···O and C-H···π interactions.

Original languageEnglish
Pages (from-to)322-335
Number of pages14
JournalSupramolecular Chemistry
Volume31
Issue number5
DOIs
StatePublished - 4 May 2019

Bibliographical note

Funding Information:
This work was supported by the Consejo Nacional de Ciencia y Tecnolog?a [CB-239581,Red Tem?tica de Qu?mica Supramolecular 281251,Sabbatical grant 121614]. This work was supported by the ?Consejo Nacional de Ciencia y Tecnolog?a (CONACyT)? under a graduate Grant (for PJGV and REEP), under a sabbatical Grant (number 121614), under Grants CB-239581 and 281251 (?Red Tem?tica de Qu?mica Supramolecular?) and under an equipment grant INFR-2014-01-225455 (for the single crystal X-ray diffractometer). Finally, access to the X-ray facilities of the Chemical Research Center at Morelos State University (LANEM) is gratefully acknowledged.

Funding Information:
This work was supported by the “Consejo Nacional de Ciencia y Tecnología (CONACyT)” under a graduate Grant (for PJGV and REEP), under a sabbatical Grant (number 121614), under Grants CB-239581 and 281251 (“Red Temática de Química Supramolecular”) and under an equipment grant INFR-2014-01-225455 (for the single crystal X-ray diffractometer). Finally, access to the X-ray facilities of the Chemical Research Center at Morelos State University (LANEM) is gratefully acknowledged.

Publisher Copyright:
© 2019, © 2019 Informa UK Limited, trading as Taylor & Francis Group.

Keywords

  • anion recognition
  • heteroditopic receptor
  • ion-pair recognition
  • polyether bridge
  • Urea

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