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Sensing a binding event through charge transport variations using an aromatic oligoamide capsule

The selective binding properties of a 13-mer oligoamide foldamer capsule composed of 4 different aromatic subunits are reported. The capsule was designed to recognize dicarboxylic acids through multiple-point interactions owing to a combination of protonation/deprotonation events, H-bonding, and geo...

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Autores principales: Mateus, Pedro, Jacquet, Antoine, Méndez-Ardoy, Alejandro, Boulloy, Alice, Kauffmann, Brice, Pecastaings, Gilles, Buffeteau, Thierry, Ferrand, Yann, Bassani, Dario M., Huc, Ivan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179446/
https://www.ncbi.nlm.nih.gov/pubmed/34163648
http://dx.doi.org/10.1039/d0sc06060g
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author Mateus, Pedro
Jacquet, Antoine
Méndez-Ardoy, Alejandro
Boulloy, Alice
Kauffmann, Brice
Pecastaings, Gilles
Buffeteau, Thierry
Ferrand, Yann
Bassani, Dario M.
Huc, Ivan
author_facet Mateus, Pedro
Jacquet, Antoine
Méndez-Ardoy, Alejandro
Boulloy, Alice
Kauffmann, Brice
Pecastaings, Gilles
Buffeteau, Thierry
Ferrand, Yann
Bassani, Dario M.
Huc, Ivan
author_sort Mateus, Pedro
collection PubMed
description The selective binding properties of a 13-mer oligoamide foldamer capsule composed of 4 different aromatic subunits are reported. The capsule was designed to recognize dicarboxylic acids through multiple-point interactions owing to a combination of protonation/deprotonation events, H-bonding, and geometrical constraints imparted by the rigidity of the foldamer backbone. Compared to tartaric acid, binding of 2,2-difluorosuccinic acid or 2,2,3,3-tetrafluorosuccinic acid resulted in symmetry breaking due to deprotonation of only one of the two carboxylic acid groups of the encapsulated species as shown by NMR studies in solution and by single-crystal X-ray diffraction in the solid state. An analogous 14-mer foldamer capsule terminated with a thiol anchoring group was used to probe the complexation event in self-assembled monolayers on Au substrates. Ellipsometry and polarization-modulation infrared absorption-reflection spectroscopy studies were consistent with the formation of a single molecule layer of the foldamer capsule oriented vertically with respect to the surface. The latter underwent smooth complexation of 2,2-difluorosuccinic acid with deprotonation of one of the two carboxylic acid groups. A significant (80-fold) difference in the charge transport properties of the monolayer upon encapsulation of the dicarboxylic acid was evidenced from conducting-AFM measurements (S = 1.1 × 10(−9)vs. 1.4 × 10(−11) ohm(−1) for the empty and complexed capsule, respectively). The modulation in conductivity was assigned to protonation of the aromatic foldamer backbone.
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spelling pubmed-81794462021-06-22 Sensing a binding event through charge transport variations using an aromatic oligoamide capsule Mateus, Pedro Jacquet, Antoine Méndez-Ardoy, Alejandro Boulloy, Alice Kauffmann, Brice Pecastaings, Gilles Buffeteau, Thierry Ferrand, Yann Bassani, Dario M. Huc, Ivan Chem Sci Chemistry The selective binding properties of a 13-mer oligoamide foldamer capsule composed of 4 different aromatic subunits are reported. The capsule was designed to recognize dicarboxylic acids through multiple-point interactions owing to a combination of protonation/deprotonation events, H-bonding, and geometrical constraints imparted by the rigidity of the foldamer backbone. Compared to tartaric acid, binding of 2,2-difluorosuccinic acid or 2,2,3,3-tetrafluorosuccinic acid resulted in symmetry breaking due to deprotonation of only one of the two carboxylic acid groups of the encapsulated species as shown by NMR studies in solution and by single-crystal X-ray diffraction in the solid state. An analogous 14-mer foldamer capsule terminated with a thiol anchoring group was used to probe the complexation event in self-assembled monolayers on Au substrates. Ellipsometry and polarization-modulation infrared absorption-reflection spectroscopy studies were consistent with the formation of a single molecule layer of the foldamer capsule oriented vertically with respect to the surface. The latter underwent smooth complexation of 2,2-difluorosuccinic acid with deprotonation of one of the two carboxylic acid groups. A significant (80-fold) difference in the charge transport properties of the monolayer upon encapsulation of the dicarboxylic acid was evidenced from conducting-AFM measurements (S = 1.1 × 10(−9)vs. 1.4 × 10(−11) ohm(−1) for the empty and complexed capsule, respectively). The modulation in conductivity was assigned to protonation of the aromatic foldamer backbone. The Royal Society of Chemistry 2021-01-22 /pmc/articles/PMC8179446/ /pubmed/34163648 http://dx.doi.org/10.1039/d0sc06060g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Mateus, Pedro
Jacquet, Antoine
Méndez-Ardoy, Alejandro
Boulloy, Alice
Kauffmann, Brice
Pecastaings, Gilles
Buffeteau, Thierry
Ferrand, Yann
Bassani, Dario M.
Huc, Ivan
Sensing a binding event through charge transport variations using an aromatic oligoamide capsule
title Sensing a binding event through charge transport variations using an aromatic oligoamide capsule
title_full Sensing a binding event through charge transport variations using an aromatic oligoamide capsule
title_fullStr Sensing a binding event through charge transport variations using an aromatic oligoamide capsule
title_full_unstemmed Sensing a binding event through charge transport variations using an aromatic oligoamide capsule
title_short Sensing a binding event through charge transport variations using an aromatic oligoamide capsule
title_sort sensing a binding event through charge transport variations using an aromatic oligoamide capsule
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179446/
https://www.ncbi.nlm.nih.gov/pubmed/34163648
http://dx.doi.org/10.1039/d0sc06060g
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