Citation: Ji-xing Yang, Li-xia Ren, Yue-sheng Li. Ring-opening Metathesis Polymerization of Cis-5-norbornene-endo-2,3-dicarboxylic Anhydride Derivatives Using the Grubbs Third Generation Catalyst[J]. Chinese Journal of Polymer Science, ;2017, 35(1): 36-45. doi: 10.1007/s10118-017-1873-1 shu

Ring-opening Metathesis Polymerization of Cis-5-norbornene-endo-2,3-dicarboxylic Anhydride Derivatives Using the Grubbs Third Generation Catalyst

School of Materials Science and Engineering and Tianjin Key Laboratory of Composite and Functional Materials, Tianjin University, Tianjin 300072, China

Corresponding author: Li-xia Ren, lxren@tju.edu.cn
Received Date: 12 August 2016
Revised Date: 9 September 2016
Accepted Date: 12 September 2016

Fund Project: the National Natural Science Foundation of China 21234006

A series of cis-5-norbornene-endo-2,3-dicarboxylic anhydride (NDCA, M1) derivatives (M2-M4) with different types of nonpolar substituted groups were synthesized and characterized by ¹H/¹³C-NMR and mass spectrometry (MS). Ring-opening metathesis polymerization (ROMP) of these monomers using the Grubbs third generation catalyst (G3) generated high molecular weight polymers with much improved solubility compared with the NDCA's homopolymer. It was found that the solubility of these polymers increased with increased substituent's steric hindrance. The living polymerization of NDCA derivative containing the bulkiest substituent (M4) catalyzed by G3 in tetrahydrofuran was confirmed by the kinetic studies with low polydispersity indices (PDI) (<1.30). By using sequential ROMP, well-defined diblock copolymers containing anhydride groups were synthesized.
- Living polymerization,
- Ring-opening metathesis polymerization,
- Amphiphilic block copolymer,
- Anhydride group
1. [1]
  Leitgeb, A., Wappel, J. and Slugovc, C., Polymer, 2010, 51:2927 doi: 10.1016/j.polymer.2010.05.002
2. [2]
  Nomura, K. and Abdellatif, M.M., Polymer, 2010, 51:1861 doi: 10.1016/j.polymer.2010.02.028
3. [3]
  Han, H.J., Zhang, S., Sun, R.Y., Wu, J.H., Xie, M.R. and Liao, X.J., Chinese J. Polym. Sci., 2016, 34:378 doi: 10.1007/s10118-016-1753-0
4. [4]
  Sutthasupa, S., Sanda, F. and Masuda, T., Macromol. Chem. Phys., 2008, 209:930 doi: 10.1002/(ISSN)1521-3935
5. [5]
  Yang, J.X., Long, Y.Y., Pan, L., Men, Y.F. and Li, Y.S., ACS Appl. Mater. Interfaces, 2016, 8:12445 doi: 10.1021/acsami.6b02073
6. [6]
  Sutthasupa, S., Terada, K., Sanda, F. and Masuda, T., Polymer, 2007, 48:3026 doi: 10.1016/j.polymer.2007.04.014
7. [7]
  Leroux, F., Pascual, S., Montembault, V. and Fontaine, L., Macromolecules, 2015, 48:3843 doi: 10.1021/acs.macromol.5b00696
8. [8]
  Lienkamp, K., Kins, C.F., Alfred, S.F., Madkour, A.E. and Tew, G.N., J. Polym. Sci., Part A:Polym. Chem., 2009, 47:1266 doi: 10.1002/pola.v47:5
9. [9]
  Sutthasupa, S., Shiotsuki, M., Matsuoka, H., Masuda, T. and Sanda, F., Macromolecules, 2010, 43:1815 doi: 10.1021/ma902405g
10. [10]
  Rawat, M., Gama, C.I., Matson, J.B. and Hsieh-Wilson, L.C., J. Am. Chem. Soc., 2008, 130:2959 doi: 10.1021/ja709993p
11. [11]
  Oh, Y.I., Sheng, G.J., Chang, S.K. and Hsieh-Wilson, L.C., Angew. Chem. Int. Ed., 2013, 52:11796 doi: 10.1002/anie.v52.45
12. [12]
  Sheng, G.J., Oh, Y.I., Chang, S.K. and Hsieh-Wilson, L.C., J. Am. Chem. Soc., 2013, 135:10898 doi: 10.1021/ja4027727
13. [13]
  Sutthasupa, S., Shiotsuki, M., Masuda, T. and Sanda, F., J. Am. Chem. Soc., 2009, 131:10546 doi: 10.1021/ja903248c
14. [14]
  Böhning, M., Goering, H., Fritz, A., Brzezinka, K.W., Turky, G., Schönhals, A. and Schartel, B., Macromolecules, 2005, 38:2764 doi: 10.1021/ma048315c
15. [15]
  Yang, D., Gao, D., Zeng, C., Jiang, J. and Xie, M., React. Funct. Polym., 2011, 71:1096 doi: 10.1016/j.reactfunctpolym.2011.08.009
16. [16]
  Zhang, M., Colby, R.H., Milner, S.T., Chung, T.C.M., Huang, T. and de Groot, W., Macromolecules, 2013, 46:4313 doi: 10.1021/ma4006632
17. [17]
  Buchmeiser, M.R., Seeber, G., Mupa, M. and Bonn, G.K., Chem. Mater., 1999, 11:1533 doi: 10.1021/cm980772i
18. [18]
  Arnauld, T., Barrett, A.G.M., Cramp, S.M., Roberts, R.S. and Zécri, F.J., Org. Lett., 2000, 2:2663 doi: 10.1021/ol006191s
19. [19]
  Buchmeiser, M.R., Atzl, N. and Bonn, G.K., J. Am. Chem. Soc., 1997, 119:9166 doi: 10.1021/ja970359w
20. [20]
  Kanaoka, S. and Grubbs, R.H., Macromolecules, 1995, 28:4707 doi: 10.1021/ma00117a050
21. [21]
  Schwab, P., Grubbs, R.H. and Ziller, J.W., J. Am. Chem. Soc., 1996, 118:100 doi: 10.1021/ja952676d
22. [22]
  Jafarpour, L., Hillier, A.C. and Nolan, S.P., Organometallics, 2002, 21:442 doi: 10.1021/om0109511
23. [23]
  Love, J.A., Morgan, J.P., Trnka, T.M. and Grubbs, R.H., Angew. Chem. Int. Ed., 2002, 41:435
24. [24]
  Paquette, L.A., Gardlik, J.M., McCullough, K.J., Samodral, R., de Lucca, G. and Ouellette, R.J., J. Am. Chem. Soc., 1983, 105:7649 doi: 10.1021/ja00364a031
25. [25]
  Okamoto, I., Ohwada, T. and Shudo, K., J. Org. Chem., 1996, 61:3155 doi: 10.1021/jo9520811
26. [26]
  Smet, M., Corens, D., van Meervelt, L. and Dehaen, W., Molecules, 2000, 5:179 doi: 10.3390/50200179
27. [27]
  Arnold, D.R. and Snow, M.S., Can. J. Chem., 1988, 66:3012 doi: 10.1139/v88-467
28. [28]
  Kira, M., Sakamoto, K. and Sakurai, H., J. Am. Chem. Soc., 1983, 105:7469 doi: 10.1021/ja00363a058
29. [29]
  Poos, G. and Lehman, M., J. Org. Chem., 1961, 26:2575 doi: 10.1021/jo01351a631
30. [30]
  Muraoka, O., Tanabe, G., Higashiura, M., Minematsu, T. and Momose, T., J. Chem. Soc., Perkin Trans. 1, 1995, 1437
31. [31]
  Fürstner, A., Ackermann, L., Gabor, B., Goddard, R., Lehmann, C.W., Mynott, R., Stelzer, F. and Thiel, O.R., Chem. Eur. J., 2001, 7:3236 doi: 10.1002/(ISSN)1521-3765
32. [32]
  Slugovc, C., Riegler, S., Hayn, G., Saf, R. and Stelzer, F., Macromol. Rapid Commun., 2003, 24:435 doi: 10.1002/marc.200390062
33. [33]
  Stubenrauch, K., Voets, I., Fritz-Popovski, G. and Trimmel, G., J. Polym. Sci., Part A:Polym. Chem., 2009, 47:1178 doi: 10.1002/pola.v47:4
34. [34]
  Alarcon, C.D.L.H., Pennadam, S. and Alexander, C., Chem. Soc. Rev., 2005, 34:276 doi: 10.1039/B406727D
35. [35]
  Stubenrauch, K., Moitzi, C., Fritz, G., Glatter, O., Trimmel, G. and Stelzer, F., Macromolecules, 2006, 39:5865 doi: 10.1021/ma060451p
36. [36]
  Yang, J.X., Cui, J., Long, Y.Y., Li, Y.G. and Li, Y.S., J. Polym. Sci., Part A:Polym. Chem., 2014, 52:2654 doi: 10.1002/pola.v52.18
37. [37]
  Cui, J., Yang, J.X., Li, Y.G. and Li, Y.S., Polymers, 2015, 7:1389 doi: 10.3390/polym7081389
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