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Tetrazine Linkers as Plug‐and‐Play Tags for General Metal‐Organic Framework Functionalization and C(60) Conjugation
The value of covalent post‐synthetic modification in expanding the chemistry and pore versatility of reticular solids is well documented. Here we use mesoporous crystals of the metal–organic framework (MOF) UiO‐68‐TZDC to demonstrate the value of tetrazine connectors for all‐purpose inverse electron...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9826395/ https://www.ncbi.nlm.nih.gov/pubmed/35972797 http://dx.doi.org/10.1002/anie.202208139 |
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author | Lerma‐Berlanga, Belén Ganivet, Carolina R. Almora‐Barrios, Neyvis Vismara, Rebecca Navarro, Jorge A. R. Tatay, Sergio Padial, Natalia M. Martí‐Gastaldo, Carlos |
author_facet | Lerma‐Berlanga, Belén Ganivet, Carolina R. Almora‐Barrios, Neyvis Vismara, Rebecca Navarro, Jorge A. R. Tatay, Sergio Padial, Natalia M. Martí‐Gastaldo, Carlos |
author_sort | Lerma‐Berlanga, Belén |
collection | PubMed |
description | The value of covalent post‐synthetic modification in expanding the chemistry and pore versatility of reticular solids is well documented. Here we use mesoporous crystals of the metal–organic framework (MOF) UiO‐68‐TZDC to demonstrate the value of tetrazine connectors for all‐purpose inverse electron‐demand Diels–Alder ligation chemistry. Our results suggest a positive effect of tetrazine reticulation over its reactivity for quantitative one‐step functionalization with a broad scope of alkene or alkyne dienophiles into pyridazine and dihydropyridazine frameworks. This permits generating multiple pore environments with diverse chemical functionalities and the expected accessible porosities, that is also extended to the synthesis of crystalline fulleretic materials by covalent conjugation of fullerene molecules. |
format | Online Article Text |
id | pubmed-9826395 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-98263952023-01-09 Tetrazine Linkers as Plug‐and‐Play Tags for General Metal‐Organic Framework Functionalization and C(60) Conjugation Lerma‐Berlanga, Belén Ganivet, Carolina R. Almora‐Barrios, Neyvis Vismara, Rebecca Navarro, Jorge A. R. Tatay, Sergio Padial, Natalia M. Martí‐Gastaldo, Carlos Angew Chem Int Ed Engl Research Articles The value of covalent post‐synthetic modification in expanding the chemistry and pore versatility of reticular solids is well documented. Here we use mesoporous crystals of the metal–organic framework (MOF) UiO‐68‐TZDC to demonstrate the value of tetrazine connectors for all‐purpose inverse electron‐demand Diels–Alder ligation chemistry. Our results suggest a positive effect of tetrazine reticulation over its reactivity for quantitative one‐step functionalization with a broad scope of alkene or alkyne dienophiles into pyridazine and dihydropyridazine frameworks. This permits generating multiple pore environments with diverse chemical functionalities and the expected accessible porosities, that is also extended to the synthesis of crystalline fulleretic materials by covalent conjugation of fullerene molecules. John Wiley and Sons Inc. 2022-09-05 2022-10-10 /pmc/articles/PMC9826395/ /pubmed/35972797 http://dx.doi.org/10.1002/anie.202208139 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Research Articles Lerma‐Berlanga, Belén Ganivet, Carolina R. Almora‐Barrios, Neyvis Vismara, Rebecca Navarro, Jorge A. R. Tatay, Sergio Padial, Natalia M. Martí‐Gastaldo, Carlos Tetrazine Linkers as Plug‐and‐Play Tags for General Metal‐Organic Framework Functionalization and C(60) Conjugation |
title | Tetrazine Linkers as Plug‐and‐Play Tags for General Metal‐Organic Framework Functionalization and C(60) Conjugation |
title_full | Tetrazine Linkers as Plug‐and‐Play Tags for General Metal‐Organic Framework Functionalization and C(60) Conjugation |
title_fullStr | Tetrazine Linkers as Plug‐and‐Play Tags for General Metal‐Organic Framework Functionalization and C(60) Conjugation |
title_full_unstemmed | Tetrazine Linkers as Plug‐and‐Play Tags for General Metal‐Organic Framework Functionalization and C(60) Conjugation |
title_short | Tetrazine Linkers as Plug‐and‐Play Tags for General Metal‐Organic Framework Functionalization and C(60) Conjugation |
title_sort | tetrazine linkers as plug‐and‐play tags for general metal‐organic framework functionalization and c(60) conjugation |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9826395/ https://www.ncbi.nlm.nih.gov/pubmed/35972797 http://dx.doi.org/10.1002/anie.202208139 |
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