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A Robust Porous Quinoline Cage: Transformation of a [4+6] Salicylimine Cage by Povarov Cyclization
Author(s) -
Alexandre PierreEmmanuel,
Zhang WenShan,
Rominger Frank,
Elbert Sven M.,
Schröder Rasmus R.,
Mastalerz Michael
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202007048
Subject(s) - cage , quinoline , covalent bond , chemistry , porosity , dynamic covalent chemistry , absorption (acoustics) , cage effect , polymer chemistry , nanotechnology , combinatorial chemistry , photochemistry , chemical engineering , organic chemistry , materials science , molecule , supramolecular chemistry , composite material , mathematics , combinatorics , engineering
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.