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

Angewandte Chemie
Pierre-Emmanuel AlexandreMichael Mastalerz

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.

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Citations

Aug 26, 2020·Chemistry : a European Journal·Martin Hähsler, Michael Mastalerz
Feb 3, 2021·Chemistry : a European Journal·Natalie SchäferFlorian Beuerle
Mar 12, 2021·Angewandte Chemie·Mingming HuaJian-Ke Sun
Apr 14, 2021·Chemistry : a European Journal·Mattes HolstenMichael Mastalerz
May 27, 2021·The Journal of Organic Chemistry·Sachie YamamotoJunpei Kuwabara
May 13, 2021·Angewandte Chemie·Eva Martínez-AhumadaMing Liu
Jun 29, 2021·Chemical Society Reviews·Hailong WangJianzhuang Jiang
Jun 5, 2021·Angewandte Chemie·Tanausú SantosRomen Carrillo
Aug 7, 2021·Organic Chemistry Frontiers : an International Journal of Organic Chemistry·Christine BourguignonMichael Mastalerz
Nov 10, 2021·Organic & Biomolecular Chemistry·Meng-Jie GuChuan-Feng Chen

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Methods Mentioned

BETA
column chromatography
NMR

Software Mentioned

PLATON
DFT
QS

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