Skip to main content
Log in

Recent advances of CuAAC click reaction in building cyclic polymer

  • Review
  • Published:
Chinese Journal of Polymer Science Aims and scope Submit manuscript

Abstract

Cyclic polymers have attracted more and more attentions in recent years because of their unique topological structures and characteristic properties in both solution and bulk state. There are relatively few reports on cyclic polymers, partly because of the more demanding synthetic procedures. In recent years, “click” reaction, especially Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC), has been widely utilized in the synthesis of cyclic polymer materials because of its high efficiency and low susceptibility to side reactions. In this review, we will focus on three aspects: (1) Constructions of monocyclic polymer using CuAAC “click” chemistry; (2) Formation of complex cyclic polymer topologies through CuAAC reactions; (3) Using CuAAC “click” reaction in the precise synthesis of molecularly defined macrocycles. We believe that the CuAAC click reaction is playing an important role in the design and synthesis of functional cyclic polymers.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Kricheldorf, H.R., J. Polym. Sci., Part A: Polym. Chem., 2010, 48(2): 251

    Article  CAS  Google Scholar 

  2. Laurent, B.A. and Grayson, S.M., Chem. Soc. Rev., 2009, 38(8): 2202

    Article  CAS  Google Scholar 

  3. Tomikawa, Y., Fukata, H., Ko, Y.S., Yamamoto, T. and Tezuka, Y., Macromolecules, 2014, 47(23): 8214

    Article  CAS  Google Scholar 

  4. Hossain, M.D., Jia, Z. and Monteiro, M.J., Macromolecules, 2014, 47(15): 4955

    Article  CAS  Google Scholar 

  5. Tezuka, Y., Polym. J., 2012, 44(12): 1159

    Article  CAS  Google Scholar 

  6. Jia, Z. and Monteiro, M.J., J. Polym. Sci., Part A: Polym. Chem., 2012, 50(11): 2085

    Article  CAS  Google Scholar 

  7. Yamamoto, T. and Tezuka, Y., Polym. Chem., 2011, 2(9): 1930

    Article  CAS  Google Scholar 

  8. Schappacher, M. and Deffieux, A., Science, 2008, 319(5869): 1512

    Article  CAS  Google Scholar 

  9. Coulembier, O., Moins, S.B., de Winter, J., Gerbaux, P., Leclére, P., Lazzaroni, R. and Dubois, P., Macromolecules, 2010, 43(1): 575

    Article  CAS  Google Scholar 

  10. Chen, R., Ling, J. and Hogen-Esch, T.E., Macromolecules, 2009, 42(16): 6015

    Article  CAS  Google Scholar 

  11. Quirk, R.P., Wang, S.F., Foster, M.D., Wesdemiotis, C. and Yol, A.M., Macromolecules, 2011, 44(19): 7538

    Article  CAS  Google Scholar 

  12. Shin, E.J., Brown, H.A., Gonzalez, S., Jeong, W., Hedrick, J.L. and Waymouth, R.M., Angew. Chem. Int. Ed. Eng., 2011, 50(28): 6388

    Article  CAS  Google Scholar 

  13. Zhang, K., Lackey, M.A., Cui, J. and Tew, G.N., J. Am. Chem. Soc., 2011, 133(11): 4140

    Article  CAS  Google Scholar 

  14. Qin, L., He, X.W., Yuan, X., Li, W.Y. and Zhang, Y.K., Anal. Bioanal. Chem., 2011, 399(10): 3375

    Article  CAS  Google Scholar 

  15. Wan, X., Liu, T. and Liu, S., Biomacromolecules, 2011, 12(4): 1146

    Article  CAS  Google Scholar 

  16. Wei, H., Chu, D.S., Zhao, J., Pahang, J.A. and Pun, S.H., ACS Macro Lett., 2013, 2(12)

    Google Scholar 

  17. Zhang, B., Zhang, H., Li, Y., Hoskins, J.N. and Grayson, S.M., ACS Macro Lett., 2013, 2(10): 845

    Article  CAS  Google Scholar 

  18. Chen, B., Jerger, K., Frechet, J.M. and Szoka, F.C., J. Control. Release, 2009, 140(3): 203

    Article  CAS  Google Scholar 

  19. Cortez, M.A., Godbey, W.T., Fang, Y., Payne, M.E., Cafferty, B.J., Kosakowska, K.A. and Grayson, S.M., J. Am. Chem. Soc., 2015, 137(20): 6541

    Article  CAS  Google Scholar 

  20. Laurent, B. and Grayson, S., J. Am. Chem. Soc., 2006, 128(13): 4238

    Article  CAS  Google Scholar 

  21. Nicolaÿ, R. and Matyjaszewski, K., Macromolecules, 2011, 44(2): 240

    Article  CAS  Google Scholar 

  22. Jeong, W., Hedrick, J.L. and Waymouth, R.M., J. Am. Chem. Soc., 2007, 129(27): 8414

    Article  CAS  Google Scholar 

  23. Boydston, A.J., Holcombe, T.W., Unruh, D.A., Fréchet, J.M. and Grubbs, R.H., J. Am. Chem. Soc., 2009, 131(15): 5388

    Article  CAS  Google Scholar 

  24. Oike, H., Imaizumi, H., Mouri, T., Yoshioka, Y., Uchibori, A. and Tezuka, Y., J. Am. Chem. Soc., 2000, 122(40): 9592

    Article  CAS  Google Scholar 

  25. Lonsdale, D.E. and Monteiro, M.J., Chem. Commun., 2010, 46(42): 7945

    Article  CAS  Google Scholar 

  26. Honda, S., Yamamoto, T. and Tezuka, Y., J. Am. Chem. Soc., 2010, 132(30): 10251

    Article  CAS  Google Scholar 

  27. Kolb, H.C., Finn, M. and Sharpless, K.B., Angew. Chem. Int. Ed., 2001, 40(11): 2004

    Article  CAS  Google Scholar 

  28. Matyjaszewski, K. and Xia, J., Chem. Rev., 2001, 101(9): 2921

    Article  CAS  Google Scholar 

  29. Chiefari, J., Chong, Y., Ercole, F., Krstina, J., Jeffery, J., Le, T.P., Mayadunne, R.T., Meijs, G.F., Moad, C.L. and Moad, G., Macromolecules, 1998, 31(16): 5559

    Article  CAS  Google Scholar 

  30. Hawker, C.J., Bosman, A.W. and Harth, E., Chem. Rev., 2001, 101(12): 3661

    Article  CAS  Google Scholar 

  31. Rosen, B.M. and Percec, V., Chem. Rev., 2009, 109(11): 5069

    Article  CAS  Google Scholar 

  32. Percec, V., Guliashvili, T., Ladislaw, J.S., Wistrand, A., Stjerndahl, A., Sienkowska, M.J., Monteiro, M.J. and Sahoo, S., J. Am. Chem. Soc., 2006, 128(43): 14156

    Article  CAS  Google Scholar 

  33. Matyjaszewski, K. and Tsarevsky, N.V., Nat. Chem., 2009, 1(4): 276

    Article  CAS  Google Scholar 

  34. Sumerlin, B.S. and Vogt, A.P., Macromolecules, 2010, 43(1): 1

    Article  CAS  Google Scholar 

  35. Hadjichristidis, N., Iatrou, H., Pitsikalis, M. and Mays, J., Prog. Polym. Sci., 2006, 31(12): 1068

    Article  CAS  Google Scholar 

  36. Qiu, X.P., Tanaka, F. and Winnik, F.M., Macromolecules, 2007, 40(20): 7069

    Article  CAS  Google Scholar 

  37. Shi, G.Y., Tang, X.Z. and Pan, C.Y., J. Polym. Sci., Part A: Polym. Chem., 2008, 46(7): 2390

    Article  CAS  Google Scholar 

  38. Zhou, F., Li, Y., Jiang, G., Zhang, Z., Tu, Y., Chen, X., Zhou, N. and Zhu, X., Polym. Chem., 2015, 6(38): 6885

    Article  CAS  Google Scholar 

  39. Zhou, F., Zhang, Z., Jiang, G., Lu, J., Chen, X., Li, Y., Zhou, N. and Zhu, X., Polym. Chem., 2016, 7(16): 2785

    Article  CAS  Google Scholar 

  40. Shi, G.Y. and Pan, C.Y., Macromol. Rapid Commun., 2008, 29(20): 1672

    Article  CAS  Google Scholar 

  41. Lonsdale, D.E., Bell, C.A. and Monteiro, M.J., Macromolecules, 2010, 43(7): 3331

    Article  CAS  Google Scholar 

  42. Ge, Z., Zhou, Y., Xu, J., Liu, H., Chen, D. and Liu, S., J. Am. Chem. Soc., 2009, 131(5): 1628

    Article  CAS  Google Scholar 

  43. Zhu, X., Zhou, N., Zhang, Z., Sun, B., Yang, Y., Zhu, J. and Zhu, X., Angew. Chem., 2011, 50(29): 6615

    Article  CAS  Google Scholar 

  44. Eugene, D.M. and Grayson, S.M., Macromolecules, 2008, 41(14): 5082

    Article  CAS  Google Scholar 

  45. Gibbons, W.M., Shannon, P.J., Sun, S.T. and Swetlin, B.J., Nature, 1991, 351(6321): 49

    Article  CAS  Google Scholar 

  46. Delaire, J.A. and Nakatani, K., Chem. Rev., 2000, 100(5): 1817

    Article  CAS  Google Scholar 

  47. Barrett, C.J., Mamiya, J.I., Yager, K.G. and Ikeda, T., Soft Matter, 2007, 3(10): 1249

    Article  CAS  Google Scholar 

  48. Wang, D., Ye, G., Zhu, Y. and Wang, X., Macromolecules, 2009, 42(7): 2651

    Article  CAS  Google Scholar 

  49. Pedersen, T.G., Johansen, P.M. and Pedersen, H.C., J. Opt. A-Pure. Appl. Op., 2000, 2(4): 272

    Article  CAS  Google Scholar 

  50. He, X., Zhang, H., Yan, D. and Wang, X., J. Polym. Sci., Part A: Polym. Chem., 2003, 41(18): 2854

    Article  CAS  Google Scholar 

  51. Rasmussen, P.H., Ramanujam, P., Hvilsted, S. and Berg, R.H., J. Am. Chem. Soc., 1999, 121(20): 4738

    Article  CAS  Google Scholar 

  52. Rochon, P., Batalla, E. and Natansohn, A., Appl. Phys. Lett., 1995, 66(2): 136

    Article  CAS  Google Scholar 

  53. Han, D., Tong, X., Zhao, Y., Galstian, T. and Zhao, Y., Macromolecules, 2010, 43(8): 3664

    Article  CAS  Google Scholar 

  54. Cai, Y., Lu, J., Zhou, F., Zhou, X., Zhou, N., Zhang, Z. and Zhu, X., Macromol. Rapid Commun., 2014, 35(9): 901

    Article  CAS  Google Scholar 

  55. Poelma, J.E., Ono, K., Miyajima, D., Aida, T., Satoh, K. and Hawker, C.J., ACS Nano, 2012, 6(12): 10845

    Article  CAS  Google Scholar 

  56. Zhang, B., Zhang, H., Elupula, R., Alb, A.M. and Grayson, S.M., Macromol. Rapid Commun., 2014, 35(2): 146

    Article  CAS  Google Scholar 

  57. Igari, M., Heguri, H., Yamamoto, T. and Tezuka, Y., Macromolecules, 2013, 46(18): 7303

    Article  CAS  Google Scholar 

  58. Tezuka, Y., Tsuchitani, A., Yoshioka, Y. and Oike, H., Macromolecules, 2003, 36(1): 65

    Article  CAS  Google Scholar 

  59. Sugai, N., Heguri, H., Ohta, K., Meng, Q., Yamamoto, T. and Tezuka, Y., J. Am. Chem. Soc., 2010, 132(42): 14790

    Article  CAS  Google Scholar 

  60. Ko, Y.S., Yamamoto, T. and Tezuka, Y., Macromol. Rapid Commun., 2014, 35(4): 412

    Article  CAS  Google Scholar 

  61. Dong, Y.Q., Tong, Y.Y., Dong, B.T., Du, F.S. and Li, Z.C., Macromolecules, 2009, 42(8): 2940

    Article  CAS  Google Scholar 

  62. Lonsdale, D.E. and Monteiro, M.J., J. Polym. Sci., Part A: Polym. Chem., 2011, 49(21): 4603

    Article  CAS  Google Scholar 

  63. Fan, X., Wang, G. and Huang, J., J. Polym. Sci., Part A: Polym. Chem., 2011, 49(6): 1361

    Article  CAS  Google Scholar 

  64. Jeong, J., Kim, K., Lee, R., Lee, S., Kim, H., Jung, H., Kadir, M.A., Jang, Y., Jeon, H.B., Matyjaszewski, K., Chang, T. and Paik, H.J., Macromolecules, 2014, 47(12): 3791

    Article  CAS  Google Scholar 

  65. Jia, Z., Lonsdale, D.E., Kulis, J. and Monteiro, M.J., ACS Macro Lett., 2012, 1(6): 780

    Article  CAS  Google Scholar 

  66. Shi, G.Y. and Pan, C.Y., J. Polym. Sci., Part A: Polym. Chem., 2009, 47(10): 2620

    Article  CAS  Google Scholar 

  67. Shi, G.Y., Sun, J.T. and Pan, C.Y., Macromol. Chem. Phys., 2011, 212(12): 1305

    Article  CAS  Google Scholar 

  68. Ge, Z., Wang, D., Zhou, Y., Liu, H. and Liu, S., Macromolecules, 2009, 42(8): 2903

    Article  CAS  Google Scholar 

  69. Peng, Y., Liu, H., Zhang, X., Liu, S. and Li, Y., Macromolecules, 2009, 42(17): 6457

    Article  CAS  Google Scholar 

  70. Kulis, J., Jia, Z. and Monteiro, M.J., Macromolecules, 2012, 45(15): 5956

    Article  CAS  Google Scholar 

  71. Sugai, N., Heguri, H., Yamamoto, T. and Tezuka, Y., J. Am. Chem. Soc., 2011, 133(49): 19694

    Article  CAS  Google Scholar 

  72. Tomikawa, Y., Yamamoto, T. and Tezuka, Y., Macromolecules, 2016, 49(11): 4076

    Article  CAS  Google Scholar 

  73. Lin, Z., Lu, P., Yu, X., Zhang, W.B., Huang, M., Wu, K., Guo, K., Wesdemiotis, C., Zhu, X., Zhang, Z., Yue, K. and Cheng, S.Z.D., Macromolecules, 2014, 47(13): 4160

    Article  CAS  Google Scholar 

  74. Li, Y., Su, H., Feng, X., Yue, K., Wang, Z., Lin, Z., Zhu, X., Fu, Q., Zhang, Z., Cheng, S.Z.D. and Zhang, W.B., Polym. Chem., 2015, 6(5): 827

    Article  CAS  Google Scholar 

  75. Zhao, J., Zhou, Y., Li, Y., Pan, X., Zhang, W., Zhou, N., Zhang, K., Zhang, Z. and Zhu, X., Polym. Chem., 2015, 6(15): 2879

    Article  CAS  Google Scholar 

  76. Wang, Y., Zhang, S., Wang, L., Zhang, W., Zhou, N., Zhang, Z. and Zhu, X., Polym. Chem., 2015, 6(25): 4669

    Article  CAS  Google Scholar 

  77. Zhang, S., Yin, L., Zhang, W., Zhang, Z. and Zhu, X., Polym. Chem., 2016, 7(11): 2112

    Article  CAS  Google Scholar 

  78. Schmidt, B.V.K.J., Fechler, N., Falkenhagen, J. and Lutz, J.F., Nat. Chem., 2011, 3(3): 234

    Article  CAS  Google Scholar 

  79. Merrifield, R.B., J. Am. Chem. Soc., 1963, 85(14): 2149

    Article  CAS  Google Scholar 

  80. Merrifield, R.B., Angew. Chem. Int. Ed., 1985, 24(10): 799

    Article  Google Scholar 

  81. Gothard, C.M., Rao, N.A. and Nowick, J.S., J. Am. Chem. Soc., 2007, 129(23): 7272

    Article  CAS  Google Scholar 

  82. Pfeifer, S., Zarafshani, Z., Badi, N. and Lutz, J.F., J. Am. Chem. Soc., 2009, 131(26): 9195

    Article  CAS  Google Scholar 

  83. Duvigneaud, V., Ressler, C., Swan, J.M., Roberts, C.W., Katsoyannis, P.G. and Gordon, S., J. Am. Chem. Soc., 1953, 75(19): 4879

    Article  CAS  Google Scholar 

  84. Muthana, S., Yu, H., Cao, H.Z., Cheng, J.S. and Chen, X., J. Org. Chem, 2009, 74(8): 2928

    Article  CAS  Google Scholar 

  85. Lu, G.L., Lam, S. and Burgess, K., Chem. Commun., 2006, (15): 1652

    Article  CAS  Google Scholar 

  86. Montagnat, O.D., Lessene, G. and Hughes, A.B., Tetrahedron Lett., 2006, 47(39): 6971

    Article  CAS  Google Scholar 

  87. Angelo, N.G. and Arora, P.S., J. Am. Chem. Soc., 2005, 127(49): 17134

    Article  CAS  Google Scholar 

  88. Paynter, O.I., Simmonds, D.J. and Whiting, M.C., J. Chem. Soc., Chem. Commun., 1982, (20): 1165

    Article  Google Scholar 

  89. Bidd, I. and Whiting, M.C., J. Chem. Soc., Chem. Commun., 1985, (9): 543

    Article  Google Scholar 

  90. Tomalia, D.A., Naylor, A.M. and Goddard, W.A., Angew. Chem. Int. Ed., 1990, 29(2): 138

    Article  Google Scholar 

  91. Zhang, J., Moore, J.S., Xu, Z. and Aguirre, R.A., J. Am. Chem. Soc., 1992, 114(6): 2273

    Article  CAS  Google Scholar 

  92. Schumm, J.S., Pearson, D.L. and Tour, J.M., Angew. Chem. Int. Ed., 1994, 33(13): 1360

    Article  Google Scholar 

  93. Hawker, C.J., Malmstrom, E.E., Frank, C.W. and Kampf, J.P., J. Am. Chem. Soc., 1997, 119(41): 9903

    Article  CAS  Google Scholar 

  94. Percec, V. and Asandei, A.D., Macromolecules, 1997, 30(25): 7701

    Article  CAS  Google Scholar 

  95. Sadighi, J.P., Singer, R.A. and Buchwald, S.L., J. Am. Chem. Soc., 1998, 120(20): 4960

    Article  CAS  Google Scholar 

  96. Louie, J. and Hartwig, J.F., Macromolecules, 1998, 31(19): 6737

    Article  CAS  Google Scholar 

  97. Martin, R.E. and Diederich, F., Angew. Chem. Int. Ed., 1999, 38(10): 1350

    Article  Google Scholar 

  98. Brooke, G.M., MacBride, J.A.H., Mohammed, S. and Whiting, M.C., Polymer, 2000, 41(17): 6457

    Article  CAS  Google Scholar 

  99. Brooke, G.M., Farren, C., Harden, A. and Whiting, M.C., Polymer, 2001, 42(7): 2777

    Article  CAS  Google Scholar 

  100. Brooke, G.M., Cameron, N.R., MacBride, J.A.H. and Whiting, M.C., Polymer, 2002, 43(4): 1139

    Article  CAS  Google Scholar 

  101. Zhou, C.Z., Liu, T.X., Xu, J.M. and Chen, Z.K., Macromolecules, 2003, 36(5): 1457

    Article  CAS  Google Scholar 

  102. Williams, J.B., Chapman, T.M. and Hercules, D.M., Macromolecules, 2003, 36(11): 3898

    Article  CAS  Google Scholar 

  103. Takizawa, K., Nulwala, H., Hu, J., Yoshinaga, K. and Hawker, C.J., J. Polym. Sci., Part A: Polym. Chem., 2008, 46(18): 5977

    Article  CAS  Google Scholar 

  104. Takizawa, K., Tang, C. and Hawker, C.J., J. Am. Chem. Soc., 2008, 130(5): 1718

    Article  CAS  Google Scholar 

  105. Binauld, S., Hawker, C.J., Fleury, E. and Drockenmuller, E., Angew. Chem. Int. Ed., 2009, 48(36): 6654

    Article  CAS  Google Scholar 

  106. Wang, Q., Qu, Y., Tian, H., Geng, Y. and Wang, F., Macromolecules, 2011, 44(6): 1256

    Article  CAS  Google Scholar 

  107. Binauld, S., Damiron, D., Connal, L.A., Hawker, C.J. and Drockenmuller, E., Macromol. Rapid Commun., 2011, 32(2): 147

    Article  CAS  Google Scholar 

  108. Koch, F.P.V., Smith, P. and Heeney, M., J. Am. Chem. Soc., 2013, 135(37): 13695

    Article  CAS  Google Scholar 

  109. Leibfarth, F.A., Johnson, J.A. and Jamison, T.F., Proc. Natl. Acad. Sci., 2015, 112(34): 10617

    Article  CAS  Google Scholar 

  110. Barnes, J.C., Ehrlich, D.J.C., Gao, A.X., Leibfarth, F.A., Jiang, Y., Zhou, E., Jamison, T.F. and Johnson, J.A., Nat. Chem., 2015, 7(10): 810

    Article  CAS  Google Scholar 

  111. Jiang, X., Lu, J., Zhou, F., Zhang, Z., Pan, X., Zhang, W., Wang, Y., Zhou, N. and Zhu, X., Polym. Chem., 2016, 7(15): 2645

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Zheng-biao Zhang  (张正彪) or Xiu-lin Zhu  (朱秀林).

Additional information

This work was financially supported by the National Natural Science Foundation of China (No. 21234005), the State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) and the Program of Innovative Research Team of Soochow University.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Huang, Zh., Zhou, Yy., Wang, Zm. et al. Recent advances of CuAAC click reaction in building cyclic polymer. Chin J Polym Sci 35, 317–341 (2017). https://doi.org/10.1007/s10118-017-1902-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10118-017-1902-0

Keywords

Navigation