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

被引：59

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

共 84 条

[11] Direct gravimetric sensing of GBL by a molecular recognition process in organic cage compounds [J].

Brutschy, Malte ;

Schneider, Markus W. ;

Mastalerz, Michael ;

Waldvogel, Siegfried R. .

CHEMICAL COMMUNICATIONS, 2013, 49 (75) :8398-8400

[12] Porous Organic Cage Compounds as Highly Potent Affinity Materials for Sensing by Quartz Crystal Microbalances [J].

Brutschy, Malte ;

Schneider, Markus W. ;

Mastalerz, Michael ;

Waldvogel, Siegfried R. .

ADVANCED MATERIALS, 2012, 24 (45) :6049-+

[13]

Christinat N., 2008, ANGEW CHEM, V120, P1874

[14]

Claridge T.D.W., 2016, High-resolution NMR techniques in organic chemistry, P61

[15] Dodecaamide Cages: Organic 12-Arm Building Blocks for Supramolecular Chemistry [J].

Culshaw, Jamie L. ;

Cheng, Ge ;

Schmidtmann, Marc ;

Hasell, Tom ;

Liu, Ming ;

Adams, Dave J. ;

Cooper, Andrew I. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (27) :10007-10010

[16] Reversible Assembly of a Supramolecular Cage Linked by Boron-Nitrogen Dative Bonds [J].

Dhara, Ayan ;

Beuerle, Florian .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (48) :17391-17396

[17] Shape-Persistent Tetrahedral [4+6] Boronic Ester Cages with Different Degrees of Fluoride Substitution [J].

Elbert, Sven M. ;

Regenauer, Nicolas I. ;

Schindler, Dorothee ;

Zhang, Wen-Shan ;

Rominger, Frank ;

Schroeder, Rasmus R. ;

Mastalerz, Michael .

CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (44) :11438-11443

[18] Boroquinol Complexes with Fused Extended Aromatic Backbones: Synthesis and Optical Properties [J].

Elbert, Sven M. ;

Wagner, Philippe ;

Kanagasundaram, Thines ;

Rominger, Frank ;

Mastalerz, Michael .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (04) :935-945

[19] Porous organic cages: soluble, modular and molecular pores [J].

Hasell, Tom ;

Cooper, Andrew I. .

NATURE REVIEWS MATERIALS, 2016, 1 (09)

[20] Solution-Processable Molecular Cage Micropores for Hierarchically Porous Materials [J].

Hasell, Tom ;

Zhang, Haifei ;

Cooper, Andrew I. .

ADVANCED MATERIALS, 2012, 24 (42) :5732-5737

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