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Vermellogens and the Development of CB[8]-Based Supramolecular Switches Using pH-Responsive and Non-Toxic Viologen Analogues
dc.contributor.author | Barravecchia Prado, Liliana Inés | |
dc.contributor.author | Blanco-Gómez, Arturo | |
dc.contributor.author | Neira, Iago | |
dc.contributor.author | Skackauskaite, Raminta | |
dc.contributor.author | Vila García, Alejandro | |
dc.contributor.author | Rey-Rico, Ana | |
dc.contributor.author | Peinador, Carlos | |
dc.contributor.author | García, Marcos D. | |
dc.date.accessioned | 2023-01-10T20:21:43Z | |
dc.date.available | 2023-01-10T20:21:43Z | |
dc.date.issued | 2022-10-07 | |
dc.identifier.citation | Liliana Barravecchia, Arturo Blanco-Gómez, Iago Neira, Raminta Skackauskaite, Alejandro Vila, Ana Rey-Rico, Carlos Peinador, and Marcos D. García. 2022. “Vermellogens” and the Development of CB[8]-Based Supramolecular Switches Using pH-Responsive and Non-Toxic Viologen Analogues. Journal of the American Chemical Society 144 (41), 19127-19136. DOI: 10.1021/jacs.2c08575 | es_ES |
dc.identifier.issn | 1520-5126 | |
dc.identifier.uri | http://hdl.handle.net/2183/32326 | |
dc.description.abstract | [Abstract] We present herein the “vermellogens”, a new class of pH-responsive viologen analogues, which replace the direct linking between para-substituted pyridinium moieties within those by a hydrazone functional group. A series of such compounds have been efficiently synthesized in aqueous media by hydrazone exchange reactions, displaying a marked pH-responsivity. Furthermore, the parent N,N′-dimethylated “vermellogen”: the “red thread”, an analogue of the herbicide paraquat and used herein as a representative model of the series, showed anion-recognition abilities, non-reversible electrochemical behavior, and non-toxicity of the modified bis-pyridinium core. The host–guest chemistry for the “red thread” with the CB[7,8] macrocyclic receptors has been extensively studied experimentally and by dispersion corrected density functional theory methods, showing a parallel behavior to that previously described for the herbicide but, crucially, swapping the well-known redox reactive capabilities of the viologen-based inclusion complexes by acid–base supramolecular responsiveness. | es_ES |
dc.description.sponsorship | This work is supported by Grants PID2019-105272GB-I00 and CTQ2017-89166-R funded by MCIN/AEI/10.13039/501100011033 and the Consellería de Educación, Universidade e Formación Profesional, Xunta de Galicia (ED431C 2018/39 and 508/2020). A.B.-G., I.N., and R.S. thank, respectively, Xunta de Galicia (ED481B-2021-099), the MECD (FPU program), and Erasmus+ program for financial support. We are very grateful for helpful discussions with Professors Hao Li (Zhejiang University), Patrice Woisel (Université de Lille) and José Luis Barriada (Universidade da Coruña). We also acknowledge the use of RIAIDT-USC analytical facilities, and CESGA (Xunta de Galicia) for computational time. | es_ES |
dc.description.sponsorship | Xunta de Galicia; ED431C 2018/39 | es_ES |
dc.description.sponsorship | Xunta de Galicia; ED431C 508/2020 | es_ES |
dc.description.sponsorship | Xunta de Galicia; ED481B-2021-099 | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | ACS | es_ES |
dc.relation | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-105272GB-I00/ES/DESARROLLO DE NUEVOS CICLOFANOS AUTOENSAMBLADOS Y SU IMPLEMENTACION EN ESTRUCTURAS NANOMETRICAS/ | es_ES |
dc.relation | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-89166-R/ES/HERRAMIENTAS PEPTIDICAS PARA APLICACIONES BIOLOGICAS: SENSORES INTELIGENTES PARA ESTUDIAR NITRACION DE PROTEINAS Y NANOMATERIALES CON FUNCIONALIDADES MODULABLES/ | es_ES |
dc.relation.uri | https://doi.org/10.1021/jacs.2c08575 | es_ES |
dc.rights | Atribución 4.0 Internacional | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | * |
dc.subject | Cations | es_ES |
dc.subject | Complexation | es_ES |
dc.subject | Potential energy | es_ES |
dc.subject | Pyridines | es_ES |
dc.subject | Titration | es_ES |
dc.title | Vermellogens and the Development of CB[8]-Based Supramolecular Switches Using pH-Responsive and Non-Toxic Viologen Analogues | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.access | info:eu-repo/semantics/openAccess | es_ES |
UDC.journalTitle | Journal of the American Chemical Society | es_ES |
UDC.volume | 144 | es_ES |
UDC.issue | 41 | es_ES |
UDC.startPage | 19127 | es_ES |
UDC.endPage | 19136 | es_ES |
dc.identifier.doi | 10.1021/jacs.2c08575 |