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Halogen‐Bonding Strapped Porphyrin BODIPY Rotaxanes for Dual Optical and Electrochemical Anion Sensing
Anion receptors employing two distinct sensory mechanisms are rare. Herein, we report the first examples of halogen‐bonding porphyrin BODIPY [2]rotaxanes capable of both fluorescent and redox electrochemical sensing of anions. (1)H NMR, UV/visible and electrochemical studies revealed rotaxane axle t...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8596797/ https://www.ncbi.nlm.nih.gov/pubmed/34319624 http://dx.doi.org/10.1002/chem.202102493 |
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author | Cheong Tse, Yuen Hein, Robert Mitchell, Edward J. Zhang, Zongyao Beer, Paul D. |
author_facet | Cheong Tse, Yuen Hein, Robert Mitchell, Edward J. Zhang, Zongyao Beer, Paul D. |
author_sort | Cheong Tse, Yuen |
collection | PubMed |
description | Anion receptors employing two distinct sensory mechanisms are rare. Herein, we report the first examples of halogen‐bonding porphyrin BODIPY [2]rotaxanes capable of both fluorescent and redox electrochemical sensing of anions. (1)H NMR, UV/visible and electrochemical studies revealed rotaxane axle triazole group coordination to the zinc(II) metalloporphyrin‐containing macrocycle component, serves to preorganise the rotaxane binding cavity and dramatically enhances anion binding affinities. Mechanically bonded, integrated‐axle BODIPY and macrocycle strapped metalloporphyrin motifs enable the anion recognition event to be sensed by the significant quenching of the BODIPY fluorophore and cathodic perturbations of the metalloporphyrin P/P(+.) redox couple. |
format | Online Article Text |
id | pubmed-8596797 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-85967972021-11-22 Halogen‐Bonding Strapped Porphyrin BODIPY Rotaxanes for Dual Optical and Electrochemical Anion Sensing Cheong Tse, Yuen Hein, Robert Mitchell, Edward J. Zhang, Zongyao Beer, Paul D. Chemistry Full Papers Anion receptors employing two distinct sensory mechanisms are rare. Herein, we report the first examples of halogen‐bonding porphyrin BODIPY [2]rotaxanes capable of both fluorescent and redox electrochemical sensing of anions. (1)H NMR, UV/visible and electrochemical studies revealed rotaxane axle triazole group coordination to the zinc(II) metalloporphyrin‐containing macrocycle component, serves to preorganise the rotaxane binding cavity and dramatically enhances anion binding affinities. Mechanically bonded, integrated‐axle BODIPY and macrocycle strapped metalloporphyrin motifs enable the anion recognition event to be sensed by the significant quenching of the BODIPY fluorophore and cathodic perturbations of the metalloporphyrin P/P(+.) redox couple. John Wiley and Sons Inc. 2021-09-06 2021-10-19 /pmc/articles/PMC8596797/ /pubmed/34319624 http://dx.doi.org/10.1002/chem.202102493 Text en © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Full Papers Cheong Tse, Yuen Hein, Robert Mitchell, Edward J. Zhang, Zongyao Beer, Paul D. Halogen‐Bonding Strapped Porphyrin BODIPY Rotaxanes for Dual Optical and Electrochemical Anion Sensing |
title | Halogen‐Bonding Strapped Porphyrin BODIPY Rotaxanes for Dual Optical and Electrochemical Anion Sensing |
title_full | Halogen‐Bonding Strapped Porphyrin BODIPY Rotaxanes for Dual Optical and Electrochemical Anion Sensing |
title_fullStr | Halogen‐Bonding Strapped Porphyrin BODIPY Rotaxanes for Dual Optical and Electrochemical Anion Sensing |
title_full_unstemmed | Halogen‐Bonding Strapped Porphyrin BODIPY Rotaxanes for Dual Optical and Electrochemical Anion Sensing |
title_short | Halogen‐Bonding Strapped Porphyrin BODIPY Rotaxanes for Dual Optical and Electrochemical Anion Sensing |
title_sort | halogen‐bonding strapped porphyrin bodipy rotaxanes for dual optical and electrochemical anion sensing |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8596797/ https://www.ncbi.nlm.nih.gov/pubmed/34319624 http://dx.doi.org/10.1002/chem.202102493 |
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