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最有效的三(3-氨基丙基)胺基缺电子三足受体用于叠氮化物。

Most Efficient Tris(3-Aminopropyl) Amine Based Electron Deficient Tripodal Receptor for Azide.

机构信息

International Research Centre, Centre for Supramolecular Chemistry, Kalasalingam University, Kalasalingam Academy of Research and Education, Anand Nagar Krishnankoil, Srivilliputtur, Tamil Nadu, 626 126, India.

Department of Chemistry, Kalasalingam University, Kalasalingam Academy of Research and Education , Anand Nagar, Krishnankoil, Srivilliputtur, Tamil Nadu, 626 126, India.

出版信息

J Fluoresc. 2020 Mar;30(2):291-300. doi: 10.1007/s10895-020-02490-6. Epub 2020 Jan 29.

DOI:10.1007/s10895-020-02490-6
PMID:31997142
Abstract

Investigation on strength of the tris(2-amino ethyl) amine and tris (3-amino propyl) amine backboned tripodal receptors, L and L (incorporated with tripodal Cν frame, thio urea-amide linkage and π-hole assisting functionality) which are premeditated to explore the prospect for a particular anion recognition are studied. UV-Vis, H- NMR, and IR spectroscopy studies indicates that both the receptors sensing azide anion, colorimetrically and binds azide anion stronger than any other anions such as acetate, and cyanide. In particular the receptor L shows the highest binding strength towards azide anion. To the best of our knowledge this is the first receptor showing highest binding ability with azide anion. We used Molecular Electrostatic Potential Surface analyses to support our spectroscopic findings. The association constant and limits of detection for receptor L with azide is found to be 8.4X10M and 3.16X10 M respectively. The observed highest binding strength of L with azide is, could be due to the cooperative effect of extended traditional hydrogen bonding via thiourea-amide functionality, anion-π interaction and Cν suitable framework.

摘要

研究了三(2-氨基乙基)胺和三(3-氨基丙基)胺支化三脚架受体 L 和 L 的强度,L 和 L (包含三脚架 Cν 框架、硫脲酰胺键和π-hole 辅助功能)旨在探索特殊阴离子识别的前景。UV-Vis、H-NMR 和 IR 光谱研究表明,这两种受体都能感应叠氮阴离子,比任何其他阴离子(如醋酸盐和氰化物)具有更强的比色和结合能力。特别是受体 L 对叠氮阴离子表现出最强的结合强度。据我们所知,这是第一个显示出与叠氮阴离子最强结合能力的受体。我们使用分子静电势表面分析来支持我们的光谱发现。发现受体 L 与叠氮的结合常数和检测限分别为 8.4×10^M 和 3.16×10^M。L 与叠氮的观察到的最高结合强度可能是由于通过硫脲酰胺功能的扩展传统氢键、阴离子-π 相互作用和 Cν 合适的框架的协同作用所致。

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本文引用的文献

1
Hydrogen bonding elements, π - hole functional moieties and Cv tripodal scaffold controlled turn-on cyanide and turn-off azide selective receptors.氢键供体、π-空穴功能部分和 Cv 三足支架控制的氰根离子开启型和叠氮离子关闭型选择性受体。
Spectrochim Acta A Mol Biomol Spectrosc. 2019 Dec 5;223:117285. doi: 10.1016/j.saa.2019.117285. Epub 2019 Jun 19.
2
Traditional hydrogen bonding donors controlled colorimetric selective anion sensing in tripodal receptors: First-naked-eye detection of cyanide by a tripodal receptor via fluoride displacement assay.传统的氢键供体控制三齿受体的比色选择性阴离子传感:通过氟离子取代实验,首例三齿受体对氰化物的肉眼检测。
Spectrochim Acta A Mol Biomol Spectrosc. 2019 Dec 5;223:117238. doi: 10.1016/j.saa.2019.117238. Epub 2019 Jun 19.
3
Electron-deficient tripodal amide based receptor: An exclusive turn-on fluorescent and colorimetric chemo sensor for cyanide ion.基于缺电子三脚架酰胺的受体:一种用于氰离子的独特开启型荧光和比色化学传感器。
Spectrochim Acta A Mol Biomol Spectrosc. 2018 Jun 5;198:309-314. doi: 10.1016/j.saa.2018.03.011. Epub 2018 Mar 9.
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Encapsulation of halides within the cavity of a pentafluorophenyl-substituted tripodal amine receptor.
Inorg Chem. 2007 Jun 11;46(12):4769-71. doi: 10.1021/ic062380g. Epub 2007 May 10.
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Synthesis and characterization of a tripodal amide ligand and its binding with anions of different dimensionality.一种三脚架状酰胺配体的合成、表征及其与不同维度阴离子的结合
Inorg Chem. 2006 May 29;45(11):4372-80. doi: 10.1021/ic052159o.
7
Influence of substituents on the strength of aryl C-H...anion hydrogen bonds.取代基对芳基C-H...阴离子氢键强度的影响。
Org Lett. 2005 Oct 27;7(22):5031-4. doi: 10.1021/ol0520119.
8
Alfred Werner revisited: the coordination chemistry of anions.重温阿尔弗雷德·维尔纳:阴离子的配位化学
Acc Chem Res. 2005 Aug;38(8):671-8. doi: 10.1021/ar040071t.
9
Anion Recognition and Sensing: The State of the Art and Future Perspectives.阴离子识别与传感:现状与未来展望。
Angew Chem Int Ed Engl. 2001 Feb 2;40(3):486-516.