A Robust Porous Quinoline Cage: Transformation of a [4+6] Salicylimine Cage by Povarov Cyclization

Porous shape‐persistent organic cages have become the object of interest in recent years because they are soluble and thus processable from solution. A variety of cages can be achieved by applying dynamic covalent chemistry (DCC), but they are less chemically stable. Here the transformation of a sal...

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Detalles Bibliográficos
Autores principales: Alexandre, Pierre‐Emmanuel, Zhang, Wen‐Shan, Rominger, Frank, Elbert, Sven M., Schröder, Rasmus R., Mastalerz, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7689861/
https://www.ncbi.nlm.nih.gov/pubmed/32521080
http://dx.doi.org/10.1002/anie.202007048
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author Alexandre, Pierre‐Emmanuel
Zhang, Wen‐Shan
Rominger, Frank
Elbert, Sven M.
Schröder, Rasmus R.
Mastalerz, Michael
author_facet Alexandre, Pierre‐Emmanuel
Zhang, Wen‐Shan
Rominger, Frank
Elbert, Sven M.
Schröder, Rasmus R.
Mastalerz, Michael
author_sort Alexandre, Pierre‐Emmanuel
collection PubMed
description Porous shape‐persistent organic cages have become the object of interest in recent years because they are soluble and thus processable from solution. A variety of cages can be achieved by applying dynamic covalent chemistry (DCC), but they are less chemically stable. Here the transformation of a salicylimine cage into a quinoline cage by a twelve‐fold Povarov reaction as the key step is described. Besides the chemical stability of the cage over a broad pH regime, it shows a unique absorption and emission depending on acid concentration. Furthermore, thin films for the vapor detection of acids were investigated, showing color switches from pale‐yellow to red, and characteristic emission profiles.
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spelling pubmed-76898612020-12-08 A Robust Porous Quinoline Cage: Transformation of a [4+6] Salicylimine Cage by Povarov Cyclization Alexandre, Pierre‐Emmanuel Zhang, Wen‐Shan Rominger, Frank Elbert, Sven M. Schröder, Rasmus R. Mastalerz, Michael Angew Chem Int Ed Engl Communications Porous shape‐persistent organic cages have become the object of interest in recent years because they are soluble and thus processable from solution. A variety of cages can be achieved by applying dynamic covalent chemistry (DCC), but they are less chemically stable. Here the transformation of a salicylimine cage into a quinoline cage by a twelve‐fold Povarov reaction as the key step is described. Besides the chemical stability of the cage over a broad pH regime, it shows a unique absorption and emission depending on acid concentration. Furthermore, thin films for the vapor detection of acids were investigated, showing color switches from pale‐yellow to red, and characteristic emission profiles. John Wiley and Sons Inc. 2020-08-07 2020-10-26 /pmc/articles/PMC7689861/ /pubmed/32521080 http://dx.doi.org/10.1002/anie.202007048 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-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Alexandre, Pierre‐Emmanuel
Zhang, Wen‐Shan
Rominger, Frank
Elbert, Sven M.
Schröder, Rasmus R.
Mastalerz, Michael
A Robust Porous Quinoline Cage: Transformation of a [4+6] Salicylimine Cage by Povarov Cyclization
title A Robust Porous Quinoline Cage: Transformation of a [4+6] Salicylimine Cage by Povarov Cyclization
title_full A Robust Porous Quinoline Cage: Transformation of a [4+6] Salicylimine Cage by Povarov Cyclization
title_fullStr A Robust Porous Quinoline Cage: Transformation of a [4+6] Salicylimine Cage by Povarov Cyclization
title_full_unstemmed A Robust Porous Quinoline Cage: Transformation of a [4+6] Salicylimine Cage by Povarov Cyclization
title_short A Robust Porous Quinoline Cage: Transformation of a [4+6] Salicylimine Cage by Povarov Cyclization
title_sort robust porous quinoline cage: transformation of a [4+6] salicylimine cage by povarov cyclization
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7689861/
https://www.ncbi.nlm.nih.gov/pubmed/32521080
http://dx.doi.org/10.1002/anie.202007048
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