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

dc.rights.licenseopenen_US
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorMATEUS, Pedro
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorJACQUET, Antoine
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorMENDEZ-ARDOY, Alejandro
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorBOULLOY, Alice
hal.structure.identifierInstitut Européen de Chimie et Biologie [IECB]
dc.contributor.authorKAUFFMANN, Brice
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorPECASTAINGS, Gilles
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorBUFFETEAU, Thierry
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorFERRAND, Yann
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorBASSANI, Dario M.
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorHUC, Ivan
dc.date.accessioned2021-07-09T15:27:09Z
dc.date.available2021-07-09T15:27:09Z
dc.date.issued2021
dc.identifier.issn2041-6520en_US
dc.identifier.otherhttps://www.rsc.org/suppdata/d0/sc/d0sc06060g/d0sc06060g1.pdfen_US
dc.identifier.otherhttps://www.rsc.org/suppdata/d0/sc/d0sc06060g/d0sc06060g2.cifen_US
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/106508
dc.description.abstractEnThe 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 x 10(-9)vs. 1.4 x 10(-11) ohm(-1) for the empty and complexed capsule, respectively). The modulation in conductivity was assigned to protonation of the aromatic foldamer backbone.
dc.description.sponsorshipLes voies de signalisation du récepteur 5-HT6: de nouvelles cibles pour le traitement de la douleur neuropathique? - ANR-19-CE18-0018en_US
dc.language.isoENen_US
dc.rightsAttribution-NonCommercial 3.0 United States*
dc.rights.urihttp://creativecommons.org/licenses/by-nc/3.0/us/*
dc.title.enSensing a binding event through charge transport variations using an aromatic oligoamide capsule
dc.typeArticle de revueen_US
dc.identifier.doi10.1039/d0sc06060g
dc.subject.halChimie/Matériauxen_US
dc.description.sponsorshipEuropeAryl amide metallofoldamersas selective saccharide sensorsen_US
bordeaux.journalChemical Scienceen_US
bordeaux.page3743-3750en_US
bordeaux.volume12en_US
bordeaux.hal.laboratoriesInstitut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN) - UMR 5248en_US
bordeaux.issue10en_US
bordeaux.institutionUniversité de Bordeauxen_US
bordeaux.institutionBordeaux INPen_US
bordeaux.institutionCNRSen_US
bordeaux.peerReviewedouien_US
bordeaux.inpressnonen_US
hal.identifierhal-03339774
hal.version1
hal.date.transferred2021-09-09T14:21:23Z
hal.exportfalse
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Chemical%20Science&rft.date=2021&rft.volume=12&rft.issue=10&rft.spage=3743-3750&rft.epage=3743-3750&rft.eissn=2041-6520&rft.issn=2041-6520&rft.au=MATEUS,%20Pedro&JACQUET,%20Antoine&MENDEZ-ARDOY,%20Alejandro&BOULLOY,%20Alice&KAUFFMANN,%20Brice&rft.genre=article


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