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Modular Synthesis of trans‐A(2)B(2)‐Porphyrins with Terminal Esters: Systematically Extending the Scope of Linear Linkers for Porphyrin‐Based MOFs

Differently functionalized porphyrin linkers represent the key compounds for the syntheses of new porphyrin‐based metal–organic frameworks (MOFs), which have gathered great interest within the last two decades. Herein we report the synthesis of a large range of 5,15‐bis(4‐ethoxycarbonylphenyl)porphy...

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Autores principales: Marschner, Stefan M., Haldar, Ritesh, Fuhr, Olaf, Wöll, Christof, Bräse, Stefan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7898653/
https://www.ncbi.nlm.nih.gov/pubmed/32857452
http://dx.doi.org/10.1002/chem.202003885
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author Marschner, Stefan M.
Haldar, Ritesh
Fuhr, Olaf
Wöll, Christof
Bräse, Stefan
author_facet Marschner, Stefan M.
Haldar, Ritesh
Fuhr, Olaf
Wöll, Christof
Bräse, Stefan
author_sort Marschner, Stefan M.
collection PubMed
description Differently functionalized porphyrin linkers represent the key compounds for the syntheses of new porphyrin‐based metal–organic frameworks (MOFs), which have gathered great interest within the last two decades. Herein we report the synthesis of a large range of 5,15‐bis(4‐ethoxycarbonylphenyl)porphyrin derivatives, through Suzuki and Sonogashira cross‐coupling reactions of an easily accessible corresponding meso‐dibrominated trans‐A(2)B(2)‐porphyrin with commercially available boronic acids or terminal alkynes. The resulting porphyrins were fully characterized through NMR, MS, and IR spectroscopy and systematically investigated through UV/Vis absorption. Finally, selected structures were saponified to the corresponding carboxylic acids and subsequently proven to be suitable for the synthesis of surface‐anchored MOF thin films.
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spelling pubmed-78986532021-03-03 Modular Synthesis of trans‐A(2)B(2)‐Porphyrins with Terminal Esters: Systematically Extending the Scope of Linear Linkers for Porphyrin‐Based MOFs Marschner, Stefan M. Haldar, Ritesh Fuhr, Olaf Wöll, Christof Bräse, Stefan Chemistry Full Papers Differently functionalized porphyrin linkers represent the key compounds for the syntheses of new porphyrin‐based metal–organic frameworks (MOFs), which have gathered great interest within the last two decades. Herein we report the synthesis of a large range of 5,15‐bis(4‐ethoxycarbonylphenyl)porphyrin derivatives, through Suzuki and Sonogashira cross‐coupling reactions of an easily accessible corresponding meso‐dibrominated trans‐A(2)B(2)‐porphyrin with commercially available boronic acids or terminal alkynes. The resulting porphyrins were fully characterized through NMR, MS, and IR spectroscopy and systematically investigated through UV/Vis absorption. Finally, selected structures were saponified to the corresponding carboxylic acids and subsequently proven to be suitable for the synthesis of surface‐anchored MOF thin films. John Wiley and Sons Inc. 2020-12-10 2021-01-18 /pmc/articles/PMC7898653/ /pubmed/32857452 http://dx.doi.org/10.1002/chem.202003885 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://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 Full Papers
Marschner, Stefan M.
Haldar, Ritesh
Fuhr, Olaf
Wöll, Christof
Bräse, Stefan
Modular Synthesis of trans‐A(2)B(2)‐Porphyrins with Terminal Esters: Systematically Extending the Scope of Linear Linkers for Porphyrin‐Based MOFs
title Modular Synthesis of trans‐A(2)B(2)‐Porphyrins with Terminal Esters: Systematically Extending the Scope of Linear Linkers for Porphyrin‐Based MOFs
title_full Modular Synthesis of trans‐A(2)B(2)‐Porphyrins with Terminal Esters: Systematically Extending the Scope of Linear Linkers for Porphyrin‐Based MOFs
title_fullStr Modular Synthesis of trans‐A(2)B(2)‐Porphyrins with Terminal Esters: Systematically Extending the Scope of Linear Linkers for Porphyrin‐Based MOFs
title_full_unstemmed Modular Synthesis of trans‐A(2)B(2)‐Porphyrins with Terminal Esters: Systematically Extending the Scope of Linear Linkers for Porphyrin‐Based MOFs
title_short Modular Synthesis of trans‐A(2)B(2)‐Porphyrins with Terminal Esters: Systematically Extending the Scope of Linear Linkers for Porphyrin‐Based MOFs
title_sort modular synthesis of trans‐a(2)b(2)‐porphyrins with terminal esters: systematically extending the scope of linear linkers for porphyrin‐based mofs
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7898653/
https://www.ncbi.nlm.nih.gov/pubmed/32857452
http://dx.doi.org/10.1002/chem.202003885
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