Cooperative Anion‐π and C−H−Cl Interactions in Multifunctional Naphthalene‐Based Receptors for Chloride Recognition: Cage‐Size Modulation Through Substitution Patterns

This study introduces a novel approach for chloride recognition utilizing multifunctional naphthalene-based receptors. By strategically modifying the substitution patterns on tetrafluoropyridines, a series of new receptors with customized cavities and enhanced binding capabilities were developed. Density functional theory (DFT) calculations and experimental studies combining NMR spectroscopy and mass spectrometry confirmed the efficacy of these receptors in capturing chloride ions. The relative chloride affinity order determined experimentally is in agreement with DFT predictions. The synergistic effect of anion-π and C-H…Cl interactions, mediated by the TFP groups, played a crucial role in achieving high binding affinity. This work provides valuable insights for designing future anion receptors with improved performance.

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Publication Details

Journal
ChemPlusChem
Published
2024-08-13
DOI
https://doi.org/10.1002/cplu.202400380
Citations
2
Primary Topic
Molecular Sensors and Ion Detection
Type
article
Field-Weighted Citation Impact
0.48

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article

Cooperative Anion‐π and C−H−Cl Interactions in Multifunctional Naphthalene‐Based Receptors for Chloride Recognition: Cage‐Size Modulation Through Substitution Patterns

Olfa Zayene, A Gaucher, Jean‐Yves Salpin, Jérôme Marrot et al.
2 citations
ChemPlusChem
Molecular Sensors and Ion Detection
0.48
article

Cooperative Anion‐π and C−H−Cl Interactions in Multifunctional Naphthalene‐Based Receptors for Chloride Recognition: Cage‐Size Modulation Through Substitution Patterns

Olfa Zayene, A Gaucher, Jean‐Yves Salpin, Jérôme Marrot, Aurélie Damond, Jun Hu, Damien Prim, Chantal Roc
article en
2 citations

Abstract

This study introduces a novel approach for chloride recognition utilizing multifunctional naphthalene-based receptors. By strategically modifying the substitution patterns on tetrafluoropyridines, a series of new receptors with customized cavities and enhanced binding capabilities were developed. Density functional theory (DFT) calculations and experimental studies combining NMR spectroscopy and mass spectrometry confirmed the efficacy of these receptors in capturing chloride ions. The relative chloride affinity order determined experimentally is in agreement with DFT predictions. The synergistic effect of anion-π and C-H…Cl interactions, mediated by the TFP groups, played a crucial role in achieving high binding affinity. This work provides valuable insights for designing future anion receptors with improved performance.

ChemPlusChemVol. 89(12)
Centre National de la Recherche Scientifique (FR), Université de Versailles Saint-Quentin-en-Yvelines (FR), Université Paris-Saclay (FR), Laboratoire Analyse et Modélisation pour la Biologie et l'Environnement (FR), CY Cergy Paris Université (FR), Institut Lavoisier de Versailles (FR), Université d'Évry Val-d'Essonne (FR)
Agence Nationale de la Recherche, Ministère de l'Enseignement Supérieur et de la Recherche, Centre National de la Recherche Scientifique
Openalex Percentile: Top 41%
Molecular Sensors and Ion Detection
0.48
DOIOpen Access PDFOpenAlex
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