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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...

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Autores principales: Lerma‐Berlanga, Belén, Ganivet, Carolina R., Almora‐Barrios, Neyvis, Vismara, Rebecca, Navarro, Jorge A. R., Tatay, Sergio, Padial, Natalia M., Martí‐Gastaldo, Carlos
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
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.
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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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