Dynamic Nucleophilic Aromatic Substitution of Tetrazines
dc.contributor.author | Santos, Tanausu | |
dc.contributor.author | Santana Rivero, David | |
dc.contributor.author | Pérez Pérez, Yaiza | |
dc.contributor.author | Martín Encinas, Endika | |
dc.contributor.author | Pasán, Jorge | |
dc.contributor.author | Hernández Daranas, Antonio | |
dc.contributor.author | Carrillo Fumero, Romen | |
dc.date.accessioned | 2024-01-24T18:46:02Z | |
dc.date.available | 2024-01-24T18:46:02Z | |
dc.date.issued | 2021-08-23 | |
dc.identifier.citation | Angewandte Chemie International Edition 60(34) : 18783-18791 (2021) | es_ES |
dc.identifier.issn | 1521-3773 | |
dc.identifier.uri | http://hdl.handle.net/10810/64309 | |
dc.description.abstract | A dynamic nucleophilic aromatic substitution of tetrazines (SNTz) is presented herein. It combines all the advantages of dynamic covalent chemistry with the versatility of the tetrazine moiety. Indeed, libraries of compounds or sophisticated molecular structures can be easily obtained, which are susceptible to post-functionalization by inverse electron demand Diels–Alder (IEDDA) reaction, which also locks the exchange. Additionally, the structures obtained can be disassembled upon the application of the right stimulus, either UV irradiation or a suitable chemical reagent. Moreover, SNTz is compatible with the imine chemistry of anilines. The high potential of this methodology has been proved by building two responsive supramolecular systems: A macrocycle that displays a light-induced release of acetylcholine; and a truncated [4+6] tetrahedral shape-persistent fluorescent cage, which is disassembled by thiols unless it is post-stabilized by IEDDA. | es_ES |
dc.description.sponsorship | This work was financially supported by Ministerio de Ciencia e Innovación (PGC2018-094503-B-C21 and MAT2017-90207-R) and by Agencia Canaria de Investigación, Innovación y Sociedad de la Información (ACIISI) (ProID2020010089). J.P. thanks Cabildo de Tenerife for the Agustín de Betancourt research position at the University of La Laguna and also Nanotec, INTech, Cabildo de Tenerife and ULL for laboratory facilities. D.S.R. thanks Ministerio de Ciencia, Innovación y Universidades for his FPU fellowship. E.M.-E. acknowledges his current contract financed by Cabildo de Tenerife, Program TF INNOVA 2016-21 (with MEDI & FDCAN Funds). All the authors thank SEGAI-ULL, and SDS-IPNA, and they are particularly grateful with Nieves M. Rodríguez and Manuel Cabrera for their technical support in this research. | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | Wiley | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICIU/PGC2018-094503-B-C21 | es_ES |
dc.relation | info:eu-repo/grantAgreement/MINECO/MAT2017-90207-R | es_ES |
dc.rights | info:eu-repo/semantics/closedAccess | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | |
dc.title | Dynamic Nucleophilic Aromatic Substitution of Tetrazines | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. | es_ES |
dc.relation.publisherversion | https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202106230 | es_ES |
dc.identifier.doi | 10.1002/anie.202106230 | |
dc.departamentoes | Química orgánica I | es_ES |
dc.departamentoeu | Kimika organikoa I | es_ES |
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This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.