Citation: Jianqiang Zhang, Yongsheng Peng, Wenguang Leng, Yanan Gao, Feifei Xu, Jinling Chai. Nitrogen ligands in two-dimensional covalent organic frameworks for metal catalysis[J]. Chinese Journal of Catalysis, ;2016, 37(4): 468-475. doi: 10.1016/S1872-2067(15)61050-6 shu

Nitrogen ligands in two-dimensional covalent organic frameworks for metal catalysis

a.
a College of Chemistry, Chemical Engineering and Material Science, Shandong Normal University, Jinan 250014, Shandong, China;
b.
b Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Corresponding author: Wenguang Leng, Jinling Chai,
Received Date: 9 December 2015
Available Online: 18 January 2016
Fund Project: 国家自然科学基金(21473196, 21403214) (21473196, 21403214) 大连理工大学精细化工国家重点实验室(KF1415). (KF1415)

We introduced bipyridine ligands into a series of two-dimensional (2D) covalent organic frameworks (COFs) using 2,2'-bipyridine-5,5'-dicarbaldehyde (2,2'-BPyDCA) as a component in the mixed building blocks. The framework of the COFs was formed by the linkage of imine groups. The ligand content in the COFs was synthetically tuned by the content of 2,2'-BPyDCA, and thus the amount of metal, palladium(II) acetate, bonded to the nitrogen ligands could be manipulated. Both the bipyridine ligands and imine groups can coordinate with Pd(II) ions, but the loading position can be varied, with one ligand favoring binding in the space between adjacent COFs' layers and the other ligand favoring binding within the pores of the COFs. The Pd(II)-loaded COFs exhibited good catalytic activity for the Heck reaction.
- Covalent organic framework,
- Metal catalysis,
- Heck reaction,
- Nitrogen ligand,
- Palladium
1. [1]
  [1] A. P. Côté, A. I. Benin, N. W. Ockwig, M. O'Keeffe, A. J. Matzger, O. M. Yaghi, Science, 2005, 310, 1166-1170.
2. [2]
  [2] H. M. El-Kaderi, J. R. Hunt, J. L. Mendoza-Cortés, A. P. Côté, R. E. Taylor, M. O'Keeffe, O. M. Yaghi, Science, 2007, 316, 268-272.
3. [3]
  [3] X. Feng, X. S. Ding, D. L. Jiang, Chem. Soc. Rev., 2012, 41, 6010-6022.
4. [4]
  [4] S. Y. Ding, W. Wang, Chem. Soc. Rev., 2013, 42, 548-568.
5. [5]
  [5] S. Y. Ding, J. Gao, Q. Wang, Y. Zhang, W. G. Song, C. Y. Su, W. Wang, J. Am. Chem. Soc., 2011, 133, 19816-19822.
6. [6]
  [6] H. Xu, X. Chen, J. Gao, J. B. Lin, M. Addicoat, S. Irle, D. L. Jiang, Chem. Commun., 2014, 50, 1292-1294.
7. [7]
  [7] P. Pachfule, S. Kandambeth, D. D. Díaz, R. Banerjee, Chem. Commun., 2014, 50, 3169-3172.
8. [8]
  [8] P. Pachfule, M. K. Panda, S. Kandambeth, S. M. Shivaprasad, D. D. Díaz, R. Banerjee, J. Mater. Chem. A, 2014, 2, 7944-7952.
9. [9]
  [9] Q. R. Fang, S. Gu, J. Zheng, Z. B. Zhuang, S. L. Qiu, Y. S. Yan, Angew. Chem. Int. Ed., 2014, 53, 2878-2882.
10. [10]
  [10] S. S. Han, H. Furukawa, O. M. Yaghi, W. A. Goddard III, J. Am. Chem. Soc., 2008, 130, 11580-11581.
11. [11]
  [11] H. Furukawa, O. M. Yaghi, J. Am. Chem. Soc., 2009, 131, 8875-8883.
12. [12]
  [12] C. J. Doonan, D. J. Tranchemontagne, T. G. Glover, J. R. Hunt, O. M. Yaghi, Nat. Chem., 2010, 2, 235-238.
13. [13]
  [13] H. P. Ma, H. Ren, S. Meng, Z. J. Yan, H. Y. Zhao, F. X. Sun, G. S. Zhu, Chem. Commun., 2013, 49, 9773-9775.
14. [14]
  [14] M. G. Rabbani, A. K. Sekizkardes, Z. Kahveci, T. E. Reich, R. S. Ding, H. M. El-Kaderi, Chem. Eur. J., 2013, 19, 3324-3328.
15. [15]
  [15] S. Dalapati, S. B. Jin, J. Gao, Y. H. Xu, A. Nagai, D. L. Jiang, J. Am. Chem. Soc., 2013, 135, 17310-17313.
16. [16]
  [16] J. Zhang, L. B. Wang, N. Li, J. F. Liu, W. Zhang, Z. B. Zhang, N. C. Zhou, X. L. Zhu, CrystEngComm, 2014, 16, 6547-6551.
17. [17]
  [17] S. Wan, J. Guo, J. Kim, H. Ihee, D. L. Jiang, Angew. Chem. Int. Ed., 2008, 47, 8826-8830.
18. [18]
  [18] S. Wan, J. Guo, J. Kim, H. Ihee, D. L. Jiang, Angew. Chem. Int. Ed., 2009, 48, 5439-5442.
19. [19]
  [19] X. Feng, L. Chen, Y. Honsho, O. Saengsawang, L. L. Liu, L. Wang, A. Saeki, S. Irle, S. Seki, Y. P. Dong, D. L. Jiang, Adv. Mater., 2012, 24, 3026-3031.
20. [20]
  [20] E. L. Spitler, J. W. Colson, F. J. Uribe-Romo, A. R. Woll, M. R. Giovino, A. Saldivar, W. R. Dichtel, Angew. Chem. Int. Ed., 2012, 51, 2623-2627.
21. [21]
  [21] M. Dogru, M. Handloser, F. Auras, T. Kunz, D. Medina, A. Hartschuh, P. Knochel, T. Bein, Angew. Chem. Int. Ed., 2013, 52, 2920-2924.
22. [22]
  [22] L. Chen, K. Furukawa, J. Gao, A. Nagai, T. Nakamura, Y. P. Dong, D. L. Jiang, J. Am. Chem. Soc., 2014, 136, 9806-9809.
23. [23]
  [23] C. R. DeBlase, K. E. Silberstein, T. T. Truong, H. D. Abruña, W. R. Dichtel, J. Am. Chem. Soc., 2013, 135, 16821-16824.
24. [24]
  [24] L. Stegbauer, K. Schwinghammer, B. V. Lotsch, Chem. Sci., 2014, 5, 2789-2793.
25. [25]
  [25] N. L. Campbell, R. Clowes, L. K. Ritchie, A. I. Cooper, Chem. Mater., 2009, 21, 204-206.
26. [26]
  [26] B. P. Biswal, S. Chandra, S. Kandambeth, B. Lukose, T. Heine, R. Banerjee, J. Am. Chem. Soc., 2013, 135, 5328-5331.
27. [27]
  [27] J. W. Colson, A. R. Woll, A. Mukherjee, M. P. Levendorf, E. L. Spitler, V. B. Shields, M. G. Spencer, J. Park, W. R. Dichtel, Science, 2011, 332, 228-231.
28. [28]
  [28] X. H. Liu, C. Z. Guan, S. Y. Ding, W. Wang, H. J. Yan, D. Wang, L. J. Wan, J. Am. Chem. Soc., 2013, 135, 10470-10474.
29. [29]
  [29] N. A. A. Zwaneveld, R. Pawlak, M. Abel, D. Catalin, D. Gigmes, D. Bertin, L. Porte, J. Am. Chem. Soc., 2008, 130, 6678-6679.
30. [30]
  [30] X. Chen, N. Huang, J. Gao, H. Xu, F. Xu, D. L. Jiang, Chem. Commun., 2014, 50, 6161-6163.
31. [31]
  [31] A. P. Côté, H. M. El-Kaderi, H. Furukawa, J. R. Hunt, O. M. Yaghi, J. Am. Chem. Soc., 2007, 129, 12914-12915.
32. [32]
  [32] L. M. Lanni, R. W. Tilford, M. Bharathy, J. J. Lavigne, J. Am. Chem. Soc., 2011, 133, 13975-13983.
33. [33]
  [33] P. Kuhn, M. Antonietti, A. Thomas, Angew. Chem. Int. Ed., 2008, 47, 3450-3453.
34. [34]
  [34] F. J. Uribe-Romo, J. R. Hunt, H. Furukawa, C. Klöck, M. O'Keeffe, O. M. Yaghi, J. Am. Chem. Soc., 2009, 131, 4570-4571.
35. [35]
  [35] F. J. Uribe-Romo, C. J. Doonan, H. Furukawa, K. Oisaki, O. M. Yaghi, J. Am. Chem. Soc., 2011, 133, 11478-11481.
36. [36]
  [36] S. Kandambeth, A. Mallick, B. Lukose, M. V. Mane, T. Heine, R. Banerjee, J. Am. Chem. Soc., 2012, 134, 19524-19527.
37. [37]
  [37] L. Y. Chen, S. Rangan, J. Li, H. F. Jiang, Y. W. Li, Green Chem., 2014, 16, 3978-3985.
38. [38]
  [38] E. D. Bloch, D. Britt, C. Lee, C. J. Doonan, F. J. Uribe-Romo, H. Furukawa, J. R. Long, O. M. Yaghi, J. Am. Chem. Soc., 2010, 132, 14382-14384.
39. [39]
  [39] A. Nagai, Z. Q. Guo, X. Feng, S. B. Jin, X. Chen, X. S. Ding, D. L. Jiang, Nat. Commun., 2011, 2, 536.
40. [40]
  [40] J. Hodačová, M. Budĕšínský, Org. Lett., 2007, 9, 5641-5643.
41. [41]
  [41] M. G. Rabbani, A. K. Sekizkardes, O. M. El-Kadri, B. R. Kaafarani, H. M. El-Kaderi, J. Mater. Chem., 2012, 22, 25409-25417.
42. [42]
  [42] X. Chen, M. Addicoat, S. Irle, A. Nagai, D. L. Jiang, J. Am. Chem. Soc., 2013, 135, 546-549.
43. [43]
  [43] The molecular size was determined by Material Studio Geometry Optimization.
44. [44]
  [44] N. Huang, Y. H. Xu, D. L. Jiang, Sci. Rep., 2014, 4, 7228.
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