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A Robust Porous Quinoline Cage: Transformation of a [4+6] Salicylimine Cage by Povarov Cyclization
Authors:Pierre-Emmanuel Alexandre  Dr Wen-Shan Zhang  Dr Frank Rominger  Dr Sven M Elbert  Prof Dr Rasmus R Schröder  Prof Dr Michael Mastalerz
Institution:1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany;2. Centre for Advanced Materials, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 225, 69120 Heidelberg, Germany;3. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

Centre for Advanced Materials, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 225, 69120 Heidelberg, Germany

Abstract: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.
Keywords:adsorption  imines  cage compounds  structure elucidation  thin films
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