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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...

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Detalles Bibliográficos
Autores principales: Cheong Tse, Yuen, Hein, Robert, Mitchell, Edward J., Zhang, Zongyao, Beer, Paul D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
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.
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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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