一种嵌有双亚胺基吡啶配体的全共轭有机聚合物材料及其在C-C偶联反应中的应用

引用本文: 陈贵夫, 王峰, 王业红, 张晓辰, 秦洪强, 邹汉法, 徐杰. 一种嵌有双亚胺基吡啶配体的全共轭有机聚合物材料及其在C-C偶联反应中的应用[J]. 催化学报, 2014, 35(4): 540-545. doi: 10.1016/S1872-2067(14)60021-8 shu

Citation: Guifu Chen, Feng Wang, Yehong Wang, Xiaochen Zhang, Hongqiang Qin, Hanfa Zou, Jie Xu. Imine-linked conjugated organic polymer bearing bis(imino)pyridine ligands and its catalytic application in C-C coupling reactions[J]. Chinese Journal of Catalysis, 2014, 35(4): 540-545. doi: 10.1016/S1872-2067(14)60021-8 shu

一种嵌有双亚胺基吡啶配体的全共轭有机聚合物材料及其在C-C偶联反应中的应用

陈贵夫 ^a,b, ,
王峰 ^{a,
,} ,
王业红 ^a, ,
张晓辰 ^a, ,
秦洪强 ^a, ,
邹汉法 ^a, ,
徐杰 ^{a,
,}

通讯作者: 王峰, 徐杰; 王峰, 徐杰

基金项目:
国家自然科学基金(21073184, 21273231) (21073184, 21273231)

中国科学院“百人计划”.

摘要: 报道了一种嵌有双亚胺基吡啶配体的全共轭有机聚合物材料. 该材料所具有的双亚胺基吡啶配体起到链接聚合物单元和络合金属中心的双重作用. 采用紫外可见光谱、红外光谱以及基质辅助激光解吸电离飞行时间质谱等对其结构进行了详细表征和确认. 由于具有全共轭结构, 该材料的热稳定性达到440 ℃, 并且在常规溶剂中较难溶解. 作为多相催化剂载体, 可以络合Pd离子形成新的多相配位催化剂, 在经典的Suzuki-Miyaura C-C偶联反应中转化率和选择性均达到99%.

关键词:

English

Imine-linked conjugated organic polymer bearing bis(imino)pyridine ligands and its catalytic application in C-C coupling reactions

1.
a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;

Corresponding author: 王峰, 徐杰; 王峰, 徐杰

Received Date: 01 November 2013
Available Online: 20 April 2014
Fund Project:
国家自然科学基金(21073184, 21273231)

中国科学院“百人计划”.

Abstract: Covalent organic polymers are an emerging class of materials with potential applications in areas including molecular separation, gas sorption, and catalysis. A novel fully conjugated organic polymer bearing bis(imino)pyridine (COP-BIP) and its catalytic function are reported here. Unlike previous COP materials, the imine bonds of COP-BIP act as both linkages and complexation sites for the binding of metal ions. A clear structure is presented based on ultraviolet-visible, Fourier transform infrared, and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry characterization. The COP-BIP materials are thermally stable up to 440 ℃ and are insoluble in conventional solvents. In addition, COP-BIP complexes Pd ions on bis(imino)pyridine sites and forms a heterogeneous catalyst, which exhibits excellent catalytic activity in the Suzuki-Miyaura C-C coupling reaction.

Key words:

1. [1] Hartley C S, Elliott E L, Moore J S. J Am Chem Soc, 2007, 129: 4512[1] Hartley C S, Elliott E L, Moore J S. J Am Chem Soc, 2007, 129: 4512
2. [2] Ding S Y, Gao J, Wang Q, Zhang Y, Song W G, Su C Y, Wang W. J Am Chem Soc, 2011, 133: 19816[2] Ding S Y, Gao J, Wang Q, Zhang Y, Song W G, Su C Y, Wang W. J Am Chem Soc, 2011, 133: 19816
3. [3] Ding X S, Guo J, Feng X, Honsho Y, Guo J D, Seki S, Maitarad P, Saeki A, Nagase S, Jiang D L. Angew Chem Int Ed, 2011, 50: 1289[3] Ding X S, Guo J, Feng X, Honsho Y, Guo J D, Seki S, Maitarad P, Saeki A, Nagase S, Jiang D L. Angew Chem Int Ed, 2011, 50: 1289
4. [4] Wan S, Guo J, Kim J, Ihee H, Jiang D L. Angew Chem Int Ed, 2008, 47: 8826[4] Wan S, Guo J, Kim J, Ihee H, Jiang D L. Angew Chem Int Ed, 2008, 47: 8826
5. [5] Wan S, Guo J, Kim J, Ihee H, Jiang D L. Angew Chem Int Ed, 2009, 48: 5439[5] Wan S, Guo J, Kim J, Ihee H, Jiang D L. Angew Chem Int Ed, 2009, 48: 5439
6. [6] Spitler E L, Colson J W, Uribe-Romo F J, Woll A R, Giovino M R, Saldivar A, Dichtel W R. Angew Chem Int Ed, 2012, 51: 2623[6] Spitler E L, Colson J W, Uribe-Romo F J, Woll A R, Giovino M R, Saldivar A, Dichtel W R. Angew Chem Int Ed, 2012, 51: 2623
7. [7] Bunck D N, Dichtel W R. Angew Chem Int Ed, 2012, 51: 1885[7] Bunck D N, Dichtel W R. Angew Chem Int Ed, 2012, 51: 1885
8. [8] Schwab M G, Fassbender B, Spiess H W, Thomas A, Feng X L, Mullen K. J Am Chem Soc, 2009, 131: 7216[8] Schwab M G, Fassbender B, Spiess H W, Thomas A, Feng X L, Mullen K. J Am Chem Soc, 2009, 131: 7216
9. [9] Choi S H, Risko C, Delgado M C R, Kim B, Bredas J L, Frisbie C D. J Am Chem Soc, 2010, 132: 4358[9] Choi S H, Risko C, Delgado M C R, Kim B, Bredas J L, Frisbie C D. J Am Chem Soc, 2010, 132: 4358
10. [10] Pandey P, Katsoulidis A P, Eryazici I, Wu Y Y, Kanatzidis M G, Nguyen S T. Chem Mater, 2010, 22: 4974[10] Pandey P, Katsoulidis A P, Eryazici I, Wu Y Y, Kanatzidis M G, Nguyen S T. Chem Mater, 2010, 22: 4974
11. [11] Uribe-Romo F J, Hunt J R, Furukawa H, Klöck C, O'Keeffe M, Yaghi O M. J Am Chem Soc, 2009, 131: 4570[11] Uribe-Romo F J, Hunt J R, Furukawa H, Klöck C, O'Keeffe M, Yaghi O M. J Am Chem Soc, 2009, 131: 4570
12. [12] Uribe-Romo F J, Doonan C J, Furukawa H, Oisaki K, Yaghi O M. J Am Chem Soc, 2011, 133: 11478[12] Uribe-Romo F J, Doonan C J, Furukawa H, Oisaki K, Yaghi O M. J Am Chem Soc, 2011, 133: 11478
13. [13] Jiang J X, Wang C, Laybourn A, Hasell T, Clowes R, Khimyak Y Z, Xiao J L, Higgins S J, Adams D J, Cooper A I. Angew Chem Int Ed, 2011, 50: 1072[13] Jiang J X, Wang C, Laybourn A, Hasell T, Clowes R, Khimyak Y Z, Xiao J L, Higgins S J, Adams D J, Cooper A I. Angew Chem Int Ed, 2011, 50: 1072
14. [14] He S, Buelt A A, Hanley J M, Morgan B P, Tennyson A G, Smith R C. Macromolecules, 2012, 45: 6344[14] He S, Buelt A A, Hanley J M, Morgan B P, Tennyson A G, Smith R C. Macromolecules, 2012, 45: 6344
15. [15] Biswal B P, Chandra S, Kandambeth S, Lukose B, Heine T, Banerjee R. J Am Chem Soc, 2013, 135: 5328[15] Biswal B P, Chandra S, Kandambeth S, Lukose B, Heine T, Banerjee R. J Am Chem Soc, 2013, 135: 5328
16. [16] Araujo C M, Doherty M D, Konezny S J, Luca O R, Usyatinsky A, Grade H, Lobkovsky E, Soloveichik G L, Crabtree R H, Batista V S. Dalton Trans, 2012, 41: 3562[16] Araujo C M, Doherty M D, Konezny S J, Luca O R, Usyatinsky A, Grade H, Lobkovsky E, Soloveichik G L, Crabtree R H, Batista V S. Dalton Trans, 2012, 41: 3562
17. [17] Tondreau A M, Lobkovsky E, Chirik P J. Org Lett, 2008, 10: 2789[17] Tondreau A M, Lobkovsky E, Chirik P J. Org Lett, 2008, 10: 2789
18. [18] Trovitch R J, Lobkovsky E, Bill E, Chirik P J. Organometallics, 2008, 27: 1470[18] Trovitch R J, Lobkovsky E, Bill E, Chirik P J. Organometallics, 2008, 27: 1470
19. [19] Hojilla Atienza C C, Bowman A C, Lobkovsky E, Chirik P J. J Am Chem Soc, 2010, 132: 16343[19] Hojilla Atienza C C, Bowman A C, Lobkovsky E, Chirik P J. J Am Chem Soc, 2010, 132: 16343
20. [20] Du W M, Wang Q F, Yu Z K. Chin J Catal (杜旺明, 王清福, 余正坤. 催化学报), 2013, 34: 1373[20] Du W M, Wang Q F, Yu Z K. Chin J Catal (杜旺明, 王清福, 余正坤. 催化学报), 2013, 34: 1373
21. [21] Ma J P, Wang M, Du Z T, Chen C, Gao J, Xu J. Polym Chem, 2012, 3: 2346[21] Ma J P, Wang M, Du Z T, Chen C, Gao J, Xu J. Polym Chem, 2012, 3: 2346
22. [22] Behrendt J M, Benstead M, Chaplin A, Wilson B, Turner M L. Macromolecules, 2011, 44: 9054[22] Behrendt J M, Benstead M, Chaplin A, Wilson B, Turner M L. Macromolecules, 2011, 44: 9054
23. [23] Qin H Q, Gao P, Wang F F, Zhao L, Zhu J, Wang A Q, Zhang T, Wu R A, Zou H F. Angew Chem Int Ed, 2011, 50: 12218[23] Qin H Q, Gao P, Wang F F, Zhao L, Zhu J, Wang A Q, Zhang T, Wu R A, Zou H F. Angew Chem Int Ed, 2011, 50: 12218
24. [24] Wu K J, Odom R W. Anal Chem, 1998, 70: 456a[24] Wu K J, Odom R W. Anal Chem, 1998, 70: 456a
25. [25] Zhang M M, M M Jiang, Liang C H. Chin J Catal (张明明, 江曼曼, 梁长海. 催化学报), 2013, 34: 2161[25] Zhang M M, M M Jiang, Liang C H. Chin J Catal (张明明, 江曼曼, 梁长海. 催化学报), 2013, 34: 2161

扫一扫看文章

计量

PDF下载量: 579
文章访问数: 1924
HTML全文浏览量: 130

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

一种嵌有双亚胺基吡啶配体的全共轭有机聚合物材料及其在C-C偶联反应中的应用

通讯作者: 王峰, 徐杰; 王峰, 徐杰

English

Imine-linked conjugated organic polymer bearing bis(imino)pyridine ligands and its catalytic application in C-C coupling reactions

Corresponding author: 王峰, 徐杰; 王峰, 徐杰

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

一种嵌有双亚胺基吡啶配体的全共轭有机聚合物材料及其在C-C偶联反应中的应用

通讯作者: 王峰, 徐杰; 王峰, 徐杰

English

Imine-linked conjugated organic polymer bearing bis(imino)pyridine ligands and its catalytic application in C-C coupling reactions

Corresponding author: 王峰, 徐杰; 王峰, 徐杰

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs