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Spatially Designed Supramolecular Anion Receptors Based on Pillar[5]arene Scaffolds: Synthesis and Halide Anion Binding Properties

[Image: see text] Urea-functionalized anion receptors based on brominated functionalized pillar[5]arenes were prepared. The binding affinity toward halide anions was investigated and probed using (1)H NMR titration and isothermal titration calorimetry (ITC). The complexation behavior was affected by...

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Autores principales: Vinodh, Mickey, Alipour, Fatemeh H., Al-Azemi, Talal F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9835175/
https://www.ncbi.nlm.nih.gov/pubmed/36643541
http://dx.doi.org/10.1021/acsomega.2c06903
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author Vinodh, Mickey
Alipour, Fatemeh H.
Al-Azemi, Talal F.
author_facet Vinodh, Mickey
Alipour, Fatemeh H.
Al-Azemi, Talal F.
author_sort Vinodh, Mickey
collection PubMed
description [Image: see text] Urea-functionalized anion receptors based on brominated functionalized pillar[5]arenes were prepared. The binding affinity toward halide anions was investigated and probed using (1)H NMR titration and isothermal titration calorimetry (ITC). The complexation behavior was affected by the structure of the receptor and the nature of the anionic guest. The synthesized receptors are highly selective toward fluoride resulting in the formation of a 1:2 host-to-guest complex. The anion receptor based on the 1,3-alternate pillar[5]arene regioisomer shows the highest affinity toward fluorine anions. No significant interactions were observed with larger bromine anions. The formation of a self-assembled supramolecular polymer driven by hydrogen bonds in solution was demonstrated by diffusion-ordered spectroscopy (DOSY), ITC, and dynamic light scattering (DLS) measurements. From ITC dilution experiments, we found that the supramolecular polymer self-assembly at higher concentrations is a spontaneous process as indicated by the positive value of Gibbs free energy (ΔG = 12.04 kJ mol(–1)).
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spelling pubmed-98351752023-01-13 Spatially Designed Supramolecular Anion Receptors Based on Pillar[5]arene Scaffolds: Synthesis and Halide Anion Binding Properties Vinodh, Mickey Alipour, Fatemeh H. Al-Azemi, Talal F. ACS Omega [Image: see text] Urea-functionalized anion receptors based on brominated functionalized pillar[5]arenes were prepared. The binding affinity toward halide anions was investigated and probed using (1)H NMR titration and isothermal titration calorimetry (ITC). The complexation behavior was affected by the structure of the receptor and the nature of the anionic guest. The synthesized receptors are highly selective toward fluoride resulting in the formation of a 1:2 host-to-guest complex. The anion receptor based on the 1,3-alternate pillar[5]arene regioisomer shows the highest affinity toward fluorine anions. No significant interactions were observed with larger bromine anions. The formation of a self-assembled supramolecular polymer driven by hydrogen bonds in solution was demonstrated by diffusion-ordered spectroscopy (DOSY), ITC, and dynamic light scattering (DLS) measurements. From ITC dilution experiments, we found that the supramolecular polymer self-assembly at higher concentrations is a spontaneous process as indicated by the positive value of Gibbs free energy (ΔG = 12.04 kJ mol(–1)). American Chemical Society 2022-12-27 /pmc/articles/PMC9835175/ /pubmed/36643541 http://dx.doi.org/10.1021/acsomega.2c06903 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Vinodh, Mickey
Alipour, Fatemeh H.
Al-Azemi, Talal F.
Spatially Designed Supramolecular Anion Receptors Based on Pillar[5]arene Scaffolds: Synthesis and Halide Anion Binding Properties
title Spatially Designed Supramolecular Anion Receptors Based on Pillar[5]arene Scaffolds: Synthesis and Halide Anion Binding Properties
title_full Spatially Designed Supramolecular Anion Receptors Based on Pillar[5]arene Scaffolds: Synthesis and Halide Anion Binding Properties
title_fullStr Spatially Designed Supramolecular Anion Receptors Based on Pillar[5]arene Scaffolds: Synthesis and Halide Anion Binding Properties
title_full_unstemmed Spatially Designed Supramolecular Anion Receptors Based on Pillar[5]arene Scaffolds: Synthesis and Halide Anion Binding Properties
title_short Spatially Designed Supramolecular Anion Receptors Based on Pillar[5]arene Scaffolds: Synthesis and Halide Anion Binding Properties
title_sort spatially designed supramolecular anion receptors based on pillar[5]arene scaffolds: synthesis and halide anion binding properties
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9835175/
https://www.ncbi.nlm.nih.gov/pubmed/36643541
http://dx.doi.org/10.1021/acsomega.2c06903
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