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
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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.
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[1]
[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
-
[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
-
[4]
[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
-
[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
-
[7]
[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
-
[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
-
[10]
[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
-
[12]
[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
-
[14]
[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
-
[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
-
[17]
[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
-
[19]
[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
-
[21]
[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
-
[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
-
[24]
[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
-
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