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

被引：56
|
作者：
Alexandre, Pierre-Emmanuel [1 ]
Zhang, Wen-Shan [2 ]
Rominger, Frank [1 ]
Elbert, Sven M. [1 ,2 ]
Schroeder, Rasmus R. [2 ]
Mastalerz, Michael [1 ,2 ]
机构：
[1] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany
[2] Heidelberg Univ, Ctr Adv Mat, Neuenheimer Feld 225, D-69120 Heidelberg, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 44期
基金：
欧洲研究理事会;
关键词：
adsorption; imines; cage compounds; structure elucidation; thin films; COVALENT ORGANIC CAGE; MOLECULAR CAGE; INTERIOR; SYMMETRY; ACID; CO2;
D O I：
10.1002/anie.202007048
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
引用
收藏
页码：19675 / 19679
页数：5
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