Citation: Li Zhou, Zhi-qiang Jiang, Na Xu, Na Liu, Zong-quan Wu. Polythiophene-block-poly(phenyl isocyanide) Copolymers:One-pot Synthesis, Properties and Applications[J]. Chinese Journal of Polymer Science, ;2017, 35(12): 1447-1456. doi: 10.1007/s10118-017-2003-9 shu

Polythiophene-block-poly(phenyl isocyanide) Copolymers:One-pot Synthesis, Properties and Applications

Department of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, and Anhui Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, Hefei University of Technology, Hefei 230009, China

Corresponding author: Na Liu, liuna@hfut.edu.cn Zong-quan Wu, zqwu@hfut.edu.cn
Received Date: 14 July 2017
Revised Date: 9 August 2017
Accepted Date: 17 August 2017

Fund Project: the National Natural Science Foundation of China 51673057the National Natural Science Foundation of China 21622402the National Natural Science Foundation of China 21574036

Conjugated block copolymers have gained increasing interests in recent years. Development of a novel method for facile synthesis of conjugated block copolymers with desired structures and functions is greatly desired. In this mini review, we summarized the recent advances in one-pot synthesis of conjugated block copolymers containing π-conjugated polythiophene and helical polyisocyanide segments by using a nickel(Ⅱ) complex as single catalyst. The sequential living polymerization of the two monomers proceeded in a controlled manner, affording expected block copolymers in high yields with controlled molecular weights (M_ns) and narrow molecular weight distributions (M_w/M_ns). By using this method, a family of block copolymers with expected structure and tunable compositions can be facilely prepared. Introducing functional groups onto the pendant, these block copolymers can exhibit interesting self-assembly property, tunable light emission and multi-responsiveness.
- Conjugated polymer,
- Helical polymer,
- Polyisocyanide,
- Block copolymer,
- Living polymerization
1. [1]
  Pauling, L., Corey, R.B. and Branson, H.R., Proc. Natl. Acad. Sci. U. S. A., 1951, 37:205 doi: 10.1073/pnas.37.4.205
2. [2]
  Watson, J.D. and Crick, F.H.C., Nature, 1953, 171:737 doi: 10.1038/171737a0
3. [3]
  Shen, J. and Okamoto, Y., Chem. Rev., 2016, 116(3):1094 doi: 10.1021/acs.chemrev.5b00317
4. [4]
  Wei, M.J., Guo, A.R. and Wu, Y.X., Acta Polymerica Sinica (in Chinese), 2017, (3):506
5. [5]
  Luo, B.J., Li, H.F., Zhang, W.Y., Zhou, C.B., Li, J.Q., Lu, C.H., He, X.H. and Jiang, S.C., Chinese J. Polym. Sci., 2017, 35(5):672 doi: 10.1007/s10118-017-1912-y
6. [6]
  Wang, R., Zhang, J. and Wan, X.H., Acta Polymerica Sinica (in Chinese), 2016, (4):409
7. [7]
  Okamoto, Y., Ohta, K.S.K., Hatada, K. and Yuki, H., J. Am. Chem. Soc., 1979, 101(16):4763 doi: 10.1021/ja00510a072
8. [8]
  Nolte, R.J.M., van Beijnen, A.J.M. and Drenth, W., J. Am. Chem. Soc., 1974, 96(18):5932 doi: 10.1021/ja00825a038
9. [9]
  Yashima, E., Ousaka, N., Taura, D., Shimomura, K., Ikai, T. and Maeda, K., Chem. Rev., 2016, 116(22):13752 doi: 10.1021/acs.chemrev.6b00354
10. [10]
  Reuther, J.F. and Novak, B.M., J. Am. Chem. Soc., 2013, 135(51):19292 doi: 10.1021/ja4098803
11. [11]
  Men, F., Zhang, J., Cui, Y.H., Zhang, L.Q. and Yue, D.M., Acta Polymerica Sinica (in Chinese), 2015, (11):1322
12. [12]
  Maeda, K., Wakasone, S., Shimomura, K., Ikai, T. and Kanoh, S., Chem. Commun., 2012, 48(27):3342 doi: 10.1039/c2cc00024e
13. [13]
  Wang, R., Li, X.F., Bai, J.W., Zhang, J., Liu, A.H. and Wan, X.H., Macromolecules, 2014, 47(5):1553 doi: 10.1021/ma500147z
14. [14]
  Wu, Z.Q., Nagai, K., Banno, M., Kento, O., Onitsuka, K. and Yashima, E., J. Am. Chem. Soc., 2009, 131(19):6708 doi: 10.1021/ja900036n
15. [15]
  Zhu, K.N., Zhu, Z.Y., Zhou, H.O., Zhang, J.Y. and Liu, S.Y., Chinese Chem. Lett., 2017, 28(6):1276 doi: 10.1016/j.cclet.2017.03.020
16. [16]
  Chen, J.L., Su, M., Jiang, Z.Q., Liu, N., Yin, J., Zhu, Y.Y. and Wu, Z.Q., Polym. Chem., 2015, 6(26):4784 doi: 10.1039/C5PY00657K
17. [17]
  Xue, Y.X., Zhu, Y.Y., Gao, L.M., He, X.Y., Liu, N., Zhang, W.Y., Yin, J., Ding, Y.S., Zhou, H.P. and Wu, Z.Q., J. Am. Chem. Soc., 2014, 136(12):4706 doi: 10.1021/ja5004747
18. [18]
  Ding, L., Huang, Y.Y., Zhang, Y.Y., Deng, J.P. and Yang, W.T., Macromolecules, 2011, 44(4):736 doi: 10.1021/ma102702a
19. [19]
  Liu, N., Ma, C.H., Sun, R.W., Huang, J., Li, C.L. and Wu, Z.Q., Polym. Chem., 2017, 8(14):2152 doi: 10.1039/C7PY00028F
20. [20]
  Yang, L., Tang, Y., Liu, N., Liu, C.H., Ding, Y.S. and Wu, Z.Q., Macromolecules, 2016, 49(20):7692 doi: 10.1021/acs.macromol.6b01870
21. [21]
  Cheerla, R. and Krishnan, M., Macromolecules, 2016, 49(2):700 doi: 10.1021/acs.macromol.5b02197
22. [22]
  Sirringhaus, H., Tessler, N. and Friend, R.H., Science, 1998, 280(5370):1741 doi: 10.1126/science.280.5370.1741
23. [23]
  Ma, W., Yang, C., Lee, K. and Heeger, A.J., Adv. Funct. Mater., 2005, 15(10):1617 doi: 10.1002/(ISSN)1616-3028
24. [24]
  Geng, J.X. and Zeng, T.Y., J. Am. Chem. Soc., 2006, 128(51):16827 doi: 10.1021/ja065035z
25. [25]
  Yang, S.J., Meng, D.L., Sun, J.H., Huang, Y., Huang, Y. and Geng, J.X., ACS Appl. Mater. Interfaces, 2014, 6(10):7686 doi: 10.1021/am500973m
26. [26]
  Deng, Y.H., Xiao, H.B., Qiao, H. and Tan, S.T., Acta Polymerica Sinica (in Chinese), 2017, (6):922
27. [27]
  McQuade, D.T., Pullen, A.E. and Swager, T.M., Chem. Rev., 2000, 100(7):2537 doi: 10.1021/cr9801014
28. [28]
  Wang, J.Y. and Pei, J., Chinese Chem. Lett., 2016, 27(8):1139 doi: 10.1016/j.cclet.2016.06.014
29. [29]
  Guo, T., Zhong, W.K., Zou, J.H., Ying, L., Yang, W. and Peng, J.B., Acta Polymerica Sinica (in Chinese), 2016, (3):360
30. [30]
  Wang, C., Dong, H., Hu, W., Liu, W. and Zhu, D., Chem. Rev., 2012, 112(4):2208 doi: 10.1021/cr100380z
31. [31]
  He, P., Qiao, X.L., Qian, Q. and Li, H.X., Chinese Chem. Lett., 2016, 27(8):1277 doi: 10.1016/j.cclet.2016.06.032
32. [32]
  Zhang, S.R., Yao, B., Zhang, Z.L., Zhang, B.H., Li, X. and Cheng, Y.X., Acta Polymerica Sinica (in Chinese), 2016, (10):1359
33. [33]
  Yan, Y.X., Yin, T.T., Liu, D.F., Liu, N., Yin, J., Zhu, Y.Y. and Wu, Z.Q., Acta Polymerica Sinica (in Chinese), 2015, (3):319
34. [34]
  Zhang, Z.Y. and Li, T., Chinese Chem. Lett., 2016, 27(8):1209 doi: 10.1016/j.cclet.2016.05.031
35. [35]
  Shao, S.Y., Ding, J.Q. and Wang, L.X., Chinese Chem. Lett., 2016, 27(8):1201 doi: 10.1016/j.cclet.2016.07.006
36. [36]
  Chang, A.P., Xie, J.D., Wu, Q.S., Chen, S.M., Du, X. and Wu, W.T., Acta Polymerica Sinica (in Chinese), 2016, (2):125
37. [37]
  Chen, W.C., Xiao, M.J., Yang, C.P., Duan, L.R. and Yang, R.Q., Chinese J. Polym. Sci., 2017, 35(2):302 doi: 10.1007/s10118-017-1892-y
38. [38]
  Foster, S., Finlayson, C.E., Keivanidis, P.E., Huang, Y.S., Hwang, I., Friend, R.H., Otten, M.B.J., Lu, L.P., Schwartz, E., Nolte, R.J.M. and Rowan, A.E., Macromolecules, 2009, 42 (6):2023 doi: 10.1021/ma801959w
39. [39]
  Su, M., Liu, N., Wang, Q., Wang, H., Yin, J. and Wu, Z.Q., Macromolecules, 2016, 49(1):110 doi: 10.1021/acs.macromol.5b02555
40. [40]
  Memon, M.A., Sun, J.H., Jung, H.T., Yan, S.K. and Geng, J.X., Chinese J. Polym. Sci., 2017, 35(3):422 doi: 10.1007/s10118-017-1895-8
41. [41]
  Higashihara, T., Ohshimizu, K., Hirao, A. and Ueda, M., Macromolecules, 2008, 41(24):9505 doi: 10.1021/ma802227r
42. [42]
  Lohwasser, R.H. and Thelakkat, M., Macromolecules, 2012, 45(7):3070 doi: 10.1021/ma2024733
43. [43]
  Hu, Y.Y., Su, M., Ma, C.H., Yu, Z.P., Liu, N., Yin, J., Ding, Y.S. and Wu, Z.Q., Macromolecules, 2015, 48(15):5204 doi: 10.1021/acs.macromol.5b01120
44. [44]
  Yu, Z.P., Ma, C.H., Wang, Q., Liu, N., Yin, J. and Wu, Z.Q., Macromolecules, 2016, 49(4):1180 doi: 10.1021/acs.macromol.5b02759
45. [45]
  Wu, Z.Q., Liu, D.F., Wang, Y., Liu, N., Yin, J., Zhu, Y.Y., Qiu, L.Z. and Ding, Y.S., Polym. Chem., 2013, 4(17):4588 doi: 10.1039/c3py00708a
46. [46]
  Zhu, Y.Y., Yin, T.T., Yin, J., Liu, N., Yu, Z.P., Zhu, Y.W., Ding, Y.S., Yin, J. and Wu, Z.Q., RSC Adv., 2014, 4(76):40241 doi: 10.1039/C4RA06571A
47. [47]
  Yu, Z.P., Liu, N., Yang, L., Jiang, Z.Q. and Wu, Z.Q., Macromolecules, 2017, 50(8):3204 doi: 10.1021/acs.macromol.6b02558
48. [48]
  Deming, T.J. and Novak, B.M., Macromolecules, 1991, 24(22):6043 doi: 10.1021/ma00022a023
49. [49]
  Onitsuka, K., Joh, T. and Takahashi, S., Angew. Chem., Int. Ed., 1992, 31(7):851 doi: 10.1002/(ISSN)1521-3773
50. [50]
  Onitsuka, K., Mori, T., Yamamoto, M., Takei, F. and Takahashi, S., Macromolecules, 2006, 39(21):7224 doi: 10.1021/ma061758r
51. [51]
  Osaka, I. and McCullough, R.D., Acc. Chem. Res., 2008, 41(9):1202 doi: 10.1021/ar800130s
52. [52]
  Yokozawa, T. and Yokoyama, A., Chem. Rev., 2009, 109(11):5595 doi: 10.1021/cr900041c
53. [53]
  Wu, Z.Q., Ono, R.J., Chen, Z., and Bielawski, C.W., J. Am. Chem. Soc., 2010, 132(40):14000 doi: 10.1021/ja106999q
54. [54]
  Wu, Z.Q., Radcliffe, J.D., Ono, R.J., Chen, Z., Li, Z.C. and Bielawski, C.W., Polym. Chem., 2012, 3(4):874 doi: 10.1039/c2py00566b
55. [55]
  Stefan, M.C., Javier, A.E., Osaka, I. and McCullough, R.D., Macromolecules, 2009, 42(1):30 doi: 10.1021/ma8020823
56. [56]
  Wu, Z.Q., Qi, C.G., Liu, N., Wang, Y., Yin, J., Zhu, Y.Y., Qiu, L.Z. and Lu, H.B., J. Polym. Sci., Part A:Polym. Chem., 2013, 51(13):2939 doi: 10.1002/pola.26689
57. [57]
  Liu, N., Qi, C.G., Wang, Y., Liu, D.F., Yin, J., Zhu, Y.Y. and Wu, Z.Q., Macromolecules, 2013, 46(19):7753 doi: 10.1021/ma4016664
58. [58]
  Su, M., Shi, S.Y., Wang, Q., Liu, N., Yin, J., Liu, C.H., Ding, Y.S. and Wu, Z.Q., Polym. Chem., 2015, 6(36):6519 doi: 10.1039/C5PY00988J
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