1,2-Disubstituted 1,2-Dihydro-1,2,4,5-tetrazine-3,6-dione as a Dynamic Covalent Bonding Unit at Room Temperature

被引：11

作者：

Kawai, Kentaro ^{[1
]}

Ikeda, Kazuki ^{[1
]}

Sato, Akane ^{[1
]}

Kabasawa, Akira ^{[2
]}

Kojima, Masahiro ^{[1
]}

Kokado, Kenta ^{[3
]}

Kakugo, Akira ^{[2
]}

Sada, Kazuki ^{[2
]}

Yoshino, Tatsuhiko ^{[1
,4
]}

Matsunaga, Shigeki ^{[1
,4
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

[2] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan

[3] Hokkaido Univ, Res Inst Elect Sci, Sapporo, Hokkaido 0010020, Japan

[4] Hokkaido Univ, Global Stn Biosurfaces & Drug Discovery, Sapporo, Hokkaido 0600812, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2022年 / 144卷 / 03期

关键词：

DIELS-ALDER REACTION; N-METHYLTRIAZOLINEDIONE; CLICK CHEMISTRY; P-URAZINE; TRIAZOLINEDIONE; POLYMER; DERIVATIVES; THERMOSETS; ULTRAFAST; TYROSINE;

D O I：

10.1021/jacs.1c11665

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dynamic covalent bonds are useful tools in a wide range of applications. Although various reversible chemical reactions have been studied for this purpose, the requirement for harsh conditions, such as high temperature and low or high pH, to activate generally stable covalent bonds limits their potential applications involving biomolecules or household utilization. Here, we report the design, synthesis, characterization, and dynamic covalent bonding properties of 1,2-disubstituted 1,2-dihydro-1,2,4,5-tetrazine-3,6-dione (TETRAD). Hetero-Diels-Alder reactions of TETRAD with furan derivatives and their retro-reactions proceeded rapidly at room temperature under neutral conditions, enabling a chemically induced sol-gel transition system.

引用

页码：1370 / 1379

页数：10

共 62 条

[21] PARA PHOTOADDITION OF N-METHYLTRIAZOLINEDIONE TO BENZENE - SYNTHESIS OF ENERGY-RICH AZO-COMPOUNDS COMPRISING BENZENE + N2 [J].

HAMROCK, SJ ;

SHERIDAN, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9247-9249

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

Hasell, Tom ;

Cooper, Andrew I. .

NATURE REVIEWS MATERIALS, 2016, 1 (09)

[23] Dynamic combinatorial/covalent chemistry: a tool to read, generate and modulate the bioactivity of compounds and compound mixtures [J].

Herrmann, Andreas .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (06) :1899-1933

[24] Exploiting furan's versatile reactivity in reversible and irreversible orthogonal peptide labeling [J].

Hoogewijs, Kurt ;

Buyst, Dieter ;

Winne, Johan M. ;

Martins, Jose C. ;

Madder, Annemieke .

CHEMICAL COMMUNICATIONS, 2013, 49 (28) :2927-2929

[25] Light-Stabilized Dynamic Materials [J].

Houck, Hannes A. ;

Blasco, Eva ;

Du Prez, Filip E. ;

Barner-Kowollik, Christopher .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (31) :12329-12337

[26] Tunable Blocking Agents for Temperature-Controlled Triazolinedione-Based Cross-Linking Reactions [J].

Houck, Hannes A. ;

De Bruycker, Kevin ;

Barner-Kowollik, Christopher ;

Winne, Johan M. ;

Du Prez, Filip E. .

MACROMOLECULES, 2018, 51 (08) :3156-3164

[27] Design of a thermally controlled sequence of triazolinedione-based click and transclick reactions [J].

Houck, Hannes A. ;

De Bruycker, Kevin ;

Billiet, Stijn ;

Dhanis, Bastiaan ;

Goossens, Hannelore ;

Catak, Saron ;

Van Speybroeck, Veronique ;

Winne, Johan M. ;

Du Prez, Filip E. .

CHEMICAL SCIENCE, 2017, 8 (04) :3098-3108

[28] By-design molecular architectures via alkyne metathesis [J].

Huang, Shaofeng ;

Lei, Zepeng ;

Jin, Yinghua ;

Zhang, Wei .

CHEMICAL SCIENCE, 2021, 12 (28) :9591-9606

[29]

Jin W, 2017, DYNAMIC COVALENT CHE

[30] Malleable and Recyclable Thermosets: The Next Generation of Plastics [J].

Jin, Yinghua ;

Lei, Zepeng ;

Taynton, Philip ;

Huang, Shaofeng ;

Zhang, Wei .

MATTER, 2019, 1 (06) :1456-1493

← 1 2 3 4 5 6 7 →