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

页码：19675 / 19679

页数：5

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