Construction of Crystalline 2D Covalent Organic Frameworks with Remarkable Chemical (Acid/Base) Stability via a Combined Reversible and Irreversible Route

被引：1651

作者：

Kandambeth, Sharath ^{[1
]}

Mallick, Arijit ^{[1
]}

Lukose, Binit ^{[2
]}

Mane, Manoj V. ^{[1
]}

Heine, Thomas ^{[2
]}

Banerjee, Rahul ^{[1
]}

机构：

[1] CSIR Nat Chem Lab, Phys Mat Chem Div, Pune 411008, Maharashtra, India

[2] Jacobs Univ Bremen, Sch Sci & Engn, Ctr Funct Nanomat, D-28759 Bremen, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 48期

关键词：

STORAGE;

D O I：

10.1021/ja308278w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two new chemically stable [acid and base] 2D crystalline covalent organic frameworks (COFs) (TpPa-1 and TpPa-2) were synthesized using combined reversible and irreversible organic reactions. Syntheses of these COFs were done by the Schiff base reactions of 1,3,5-triformylphloroglucinol (Tp) with p-phenylenediamine (Pa-1) and 2,5-dimethyl-p-phenylenediamine (Pa-2), respectively, in 1:1 mesitylene/dioxane. The expected enol-imine (OH) form underwent irreversible proton tautomerism, and only the keto-enamine form was observed. Because of the irreversible nature of the total reaction and the absence of an imine bond in the system, TpPa-1 and TpPa-2 showed strong resistance toward acid (9 N HCl) and boiling water. Moreover, TpPa-2 showed exceptional stability in base (9 N NaOH) as well.

引用

页码：19524 / 19527

页数：4

共 21 条

[1] Targeted Synthesis of a Porous Aromatic Framework with High Stability and Exceptionally High Surface Area [J].

Ben, Teng ;

Ren, Hao ;

Ma, Shengqian ;

Cao, Dapeng ;

Lan, Jianhui ;

Jing, Xiaofei ;

Wang, Wenchuan ;

Xu, Jun ;

Deng, Feng ;

Simmons, Jason M. ;

Qiu, Shilun ;

Zhu, Guangshan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (50) :9457-9460

[2] Highly stable keto-enamine salicylideneanilines [J].

Chong, JH ;

Sauer, M ;

Patrick, BO ;

MacLachlan, MJ .

ORGANIC LETTERS, 2003, 5 (21) :3823-3826

[3] Porous, crystalline, covalent organic frameworks [J].

Côté, AP ;

Benin, AI ;

Ockwig, NW ;

O'Keeffe, M ;

Matzger, AJ ;

Yaghi, OM .

SCIENCE, 2005, 310 (5751) :1166-1170

[4] Isoreticular Two-Dimensional Covalent Organic Frameworks Synthesized by On-Surface Condensation of Diboronic Acids [J].

Dienstmaier, Juergen F. ;

Medina, Dana D. ;

Dogru, Mirjam ;

Knochel, Paul ;

Bein, Thomas ;

Heckl, Wolfgang M. ;

Lackinger, Markus .

ACS NANO, 2012, 6 (08) :7234-7242

[5] Construction of Covalent Organic Framework for Catalysis: Pd/COF-LZU1 in Suzuki-Miyaura Coupling Reaction [J].

Ding, San-Yuan ;

Gao, Jia ;

Wang, Qiong ;

Zhang, Yuan ;

Song, Wei-Guo ;

Su, Cheng-Yong ;

Wang, Wei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) :19816-19822

[6] An n-Channel Two-Dimensional Covalent Organic Framework [J].

Ding, Xuesong ;

Chen, Long ;

Honsho, Yoshihito ;

Feng, Xiao ;

Saenpawang, Oraphan ;

Guo, Jingdong ;

Saeki, Akinori ;

Seki, Shu ;

Irle, Stephan ;

Nagase, Shigeru ;

Parasuk, Vudhichai ;

Jiang, Donglin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (37) :14510-14513

[7] Experimental and computational studies of pyridine-assisted post-synthesis modified air stable covalent-organic frameworks [J].

Du, Yi ;

Mao, Kanmi ;

Kamakoti, Preeti ;

Ravikovitch, Peter ;

Paur, Charanjit ;

Cundy, Stephen ;

Li, Quanchang ;

Calabro, David .

CHEMICAL COMMUNICATIONS, 2012, 48 (38) :4606-4608

[8] Covalent organic frameworks [J].

Feng, Xiao ;

Ding, Xuesong ;

Jiang, Donglin .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (18) :6010-6022

[9] Storage of Hydrogen, Methane, and Carbon Dioxide in Highly Porous Covalent Organic Frameworks for Clean Energy Applications [J].

Furukawa, Hiroyasu ;

Yaghi, Omar M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) :8875-8883

[10]

Heine T., 2009, DEMON NANO

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