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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Main Authors: Alexandre, Pierre-Emmanuel (Author) , Zhang, Wen-Shan (Author) , Rominger, Frank (Author) , Elbert, Sven (Author) , Schröder, Rasmus R. (Author) , Mastalerz, Michael (Author)
Format: Article (Journal)
Language:English
Published: 2020
In: Angewandte Chemie. International edition
Year: 2020, Volume: 59, Issue: 44, Pages: 19675-19679
ISSN:1521-3773
DOI:10.1002/anie.202007048
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/anie.202007048
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202007048
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Author Notes:Pierre-Emmanuel Alexandre, Wen-Shan Zhang, Frank Rominger, Sven M. Elbert, Rasmus R. Schröder, and Michael Mastalerz
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Summary: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.
Item Description:First published: 10 June 2020
Gesehen am 02.11.2021
Physical Description:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.202007048