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用于氯离子识别的多功能萘基受体中协同的阴离子-π和C-H-Cl相互作用：通过取代模式调节笼尺寸

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

作者信息

Zayene Olfa, Hu Jun, Damond Aurélie, Roc Chantal, Marrot Jérôme, Gaucher Anne, Salpin Jean-Yves, Prim Damien

机构信息

Université Paris-Saclay, UVSQ, CNRS, Institut Lavoisier de Versailles, 78035, Versailles cedex, France.

Université Paris-Saclay, Univ Evry, CY Cergy Paris Université, CNRS, LAMBE, 91025, Evry-Courcouronnes, France.

出版信息

Chempluschem. 2024 Dec;89(12):e202400380. doi: 10.1002/cplu.202400380. Epub 2024 Oct 21.

DOI:10.1002/cplu.202400380
PMID:39136597
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11639634/
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.

摘要

本研究介绍了一种利用多功能萘基受体识别氯离子的新方法。通过策略性地改变四氟吡啶上的取代模式，开发了一系列具有定制空腔和增强结合能力的新型受体。密度泛函理论（DFT）计算以及结合核磁共振光谱和质谱的实验研究证实了这些受体捕获氯离子的功效。实验确定的相对氯离子亲和力顺序与DFT预测结果一致。由TFP基团介导的阴离子-π和C-H…Cl相互作用的协同效应在实现高结合亲和力方面发挥了关键作用。这项工作为设计性能更优的未来阴离子受体提供了有价值的见解。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e47/11639634/d3c3677acb7e/CPLU-89-e202400380-g012.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e47/11639634/0a375d72f7a7/CPLU-89-e202400380-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e47/11639634/5b070b463f9d/CPLU-89-e202400380-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e47/11639634/d3c3677acb7e/CPLU-89-e202400380-g012.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e47/11639634/191bf98da194/CPLU-89-e202400380-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e47/11639634/dae0a827b790/CPLU-89-e202400380-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e47/11639634/e09dd343eaaa/CPLU-89-e202400380-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e47/11639634/aa0b96358fdb/CPLU-89-e202400380-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e47/11639634/f62d6ce211e8/CPLU-89-e202400380-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e47/11639634/0a375d72f7a7/CPLU-89-e202400380-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e47/11639634/5b070b463f9d/CPLU-89-e202400380-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e47/11639634/d3c3677acb7e/CPLU-89-e202400380-g012.jpg

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本文引用的文献

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