Synthesis and MALDI-TOF Characterization of -CD Core ATRP Initiators and RAFT Chain Transfers with Different Degrees of Substitution

注册 English

Synthesis and MALDI-TOF Characterization of -CD Core ATRP Initiators and RAFT Chain Transfers with Different Degrees of Substitution

Yan Xin , Hong Wang , Bo-wen Liu , Jin-ying Yuan

Citation: Yan Xin, Hong Wang, Bo-wen Liu, Jin-ying Yuan. Synthesis and MALDI-TOF Characterization of -CD Core ATRP Initiators and RAFT Chain Transfers with Different Degrees of Substitution[J]. Chinese Journal of Polymer Science, 2015, 33(1): 36-48. doi: 10.1007/s10118-015-1572-8 shu

shu

Synthesis and MALDI-TOF Characterization of -CD Core ATRP Initiators and RAFT Chain Transfers with Different Degrees of Substitution

1.
Key Lab of Organic Optoelectronics and Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China

通讯作者: Jin-ying Yuan,

基金项目:
This work was financially supported by the National Natural Science Foundation of China (Nos. 21174076 and 21374053).

摘要: In this paper, three different kinds of -CD derivatives were synthesized as atom transfer radical polymerization (ATRP) initiator or reversible addition-fragmentation chain transfer polymerization (RAFT) chain transfers. The degree of substitution for each derivative was carefully characterized through 1H-NMR, 13C-NMR spectroscopy and matrix-assisted laser desorption/ionization time of flight mass spectrometry (MALDI-TOF-MS). The factors influencing the degree of substitution were discussed. Moreover, the comparison between ATRP and RAFT was shown in the polymerization of N-isopropyl acrylamide (NIPAM).

关键词:

English

Synthesis and MALDI-TOF Characterization of -CD Core ATRP Initiators and RAFT Chain Transfers with Different Degrees of Substitution

1.
Key Lab of Organic Optoelectronics and Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China

Corresponding author: Jin-ying Yuan,

Received Date: 17 March 2014
Revised Date: 04 May 2014
Available Online: 05 January 2015
Fund Project:
This work was financially supported by the National Natural Science Foundation of China (Nos. 21174076 and 21374053).

Abstract: In this paper, three different kinds of -CD derivatives were synthesized as atom transfer radical polymerization (ATRP) initiator or reversible addition-fragmentation chain transfer polymerization (RAFT) chain transfers. The degree of substitution for each derivative was carefully characterized through 1H-NMR, 13C-NMR spectroscopy and matrix-assisted laser desorption/ionization time of flight mass spectrometry (MALDI-TOF-MS). The factors influencing the degree of substitution were discussed. Moreover, the comparison between ATRP and RAFT was shown in the polymerization of N-isopropyl acrylamide (NIPAM).

Key words:

1. [1]
  Durr, C.J., Hlalele, L., Kaiser, A., Brandau, S. and Barner-Kowollik, C., Macromolecules, 2013, 46: 49
2. [2]
  Gunay, K.A., Theato, P. and Klok, H.A., J. Polym. Sci., Part A: Polym. Chem., 2013, 51: 1
3. [3]
  Sabadini, E., Fdo, C.E. and Cosgrove, T., Langmuir, 2013, 29: 4664
4. [4]
  Wang, K., Peng, H., Thurecht, K.J., Puttick, S. and Whittaker, A., Polym. Chem., 2013, 4: 4480
5. [5]
  Zhang, M., Xiong, Q., Chen, J., Wang, Y. and Zhang, Q., Polym. Chem., 2013, 4: 5086
6. [6]
  Kim, D.G., Kang, H., Choi, Y.S., Han, S. and Lee, J.C., Polym. Chem., 2013, 4: 5065
7. [7]
  Ratkanthwar, K., Hadjichristidis, N., Lee, S., Chang, T., Pudukulathan, Z. and Vlassopoulos, D., Polym. Chem., 2013, 4: 5645
8. [8]
  Zhang, Y., Li, H., Dong, J.Y. and Hu, Y., Polym. Chem., 2014, 5: 105
9. [9]
  Hadjichristidis. N., Zhao, H., Alkayal, N. and Gnanou, Y., Chem. Commun., 2013, 49: 8952
10. [10]
  Zhao, Y.C., Zhang, L.M., Wang, T. and Han, B.H., Polym. Chem., 2014, 5: 614
11. [11]
  Altintas, Vogt, A.P., Barner-Kowollik, C. and Tunca, U., Polym. Chem., 2012, 3: 34
12. [12]
  Yuan, W., Zhao, Z., Yuan, J., Gu, S., Zhang, F., Xie, X. and Ren, J., Polym. Int., 2011, 60: 194
13. [13]
  Chang, S.K., Zeng, C., Li, J.B. and Ren, J., Polym. Int., 2012, 61: 1492
14. [14]
  Wu, W.B., Fu, Y.J., Wang, C., Xu, Z., Ye, C., Qin, J.G. and Li, Z., Chinese J. Polym. Sci., 2013, 31(10): 1415
15. [15]
  Cheng, G.W., Fan, X.D., Tian, W., Liu, Y.Y. and Kong, J.E., Polym. Int., 2010, 59: 543
16. [16]
  Liu, F., Wan, D. and Tang, T., Chinese J. Polym. Sci., 2014, 32(1): 51
17. [17]
  Wang, T.L., Huang, F.J. and Lee, S.W., Polym. Int., 2002, 51: 1348
18. [18]
  Zhang, B., Li, Y.P., Sun, J.H., Wang, S.W., Zhao, Y.L. and Wu, Z.Y., Polym. Int., 2009, 58: 752
19. [19]
  Zheng, Q., Zheng, G.H. and Pan, C.Y., Polym. Int., 2006, 55: 1114
20. [20]
  Hong, C.Y., You, Y.Z., Liu, J. and Pan, C.Y., J. Polym. Sci., Part A: Polym. Chem., 2005, 43: 6379
21. [21]
  Gong, F., Cheng, X., Wang, S., Wang, Y., Gao, Y. and Cheng, S., Polymer, 2009, 50: 2775
22. [22]
  Li, X., Hong, C.Y. and Pan, C.Y., Polymer, 2010, 51: 92
23. [23]
  Liu, W., Liu, R. G., Li, Y., Wang, W., Ma, L., Wu, M. and Huang, Y., Polymer, 2009, 50: 2716
24. [24]
  Viglianisi, C., Menichetti, S., Assanelli, G., Sacchi, M.C., Tritto, I. and Losio, S., J. Polym. Sci., Part A: Polym. Chem., 2012, 50: 4647
25. [25]
  Twibanire, J.D.K. and Grindley, T.B., Polymer, 2012, 4: 794
26. [26]
  Jiang, X.B., Zhu, W., Yan, Y.C., Chen, Y.M. and Xi, F., React. Funct. Polym., 2011, 71: 843
27. [27]
  Rikkou, M.D. and Patrickios, C.S., Prog. Polym. Sci., 2011, 36: 1079
28. [28]
  Iskin, B., Yilmaz, G. and Yagci, Y., Polym. Chem., 2011, 2: 2865
29. [29]
  Blanazs, Madsen, J., Battaglia, G., Ryan, A.J. and Armes, S.P., J. Am. Chem. Soc., 2011, 133: 16581
30. [30]
  Ishizu, K., Shibuya, T. and Mori, A., Polym. Int., 2002, 51: 424
31. [31]
  Ishizu, K., Shibuya, T., Park, J.B. and Uchida, S., Polym. Int., 2004, 53: 259
32. [32]
  Ishizu, K., Takashimizu, C., Shibuya, T. and Uchida, S., Polym. Int., 2003, 52: 1010
33. [33]
  Ju, M.J., Shen, L., Gong, F.R., Gao, Y. and Zhang, W.A., Polym. Int., 2012, 61: 1447
34. [34]
  Kowalczuk, Kronek, J., Bosowska, K., Trzebicka, B. and Dworak, A., Polym. Int., 2011, 60: 1001
35. [35]
  Lou, L.P., Jiang, L.M., Liu, J.Z., Sun, W.L. and Shen, Z.Q., Polym. Int., 2007, 56: 796
36. [36]
  Tanghe, L.M., Goethals, E.J. and Prez, F.D., Polym. Int., 2003, 52: 191
37. [37]
  Taton, D., Gnanou, Y., Matmour, R., Angot, S., Hou, S., Francis, R., Lepoittevin, B., Moinard, D. and Babin, J., Polym. Int., 2006, 55: 1138
38. [38]
  Wang, T.L. and Tseng, C.G., Polym. Int., 2006, 55: 558
39. [39]
  Zhang, X., Chen, Y.M., Gong, A.J., Chen, C.F. and Xi, F., Polym. Int., 1999, 48: 896
40. [40]
  Liu, W., Liu, Y., Hao, X., Zeng, G., Wang, W., Liu, R. and Huang, Y., Carbohydr. Polym., 2012, 88: 290
41. [41]
  Wang, K., Cai, L. and Wang, S., Polymer, 2011, 52: 2827
42. [42]
  Mathapa, B. G. and Paunov, V.N., Soft Matter, 2013, 9: 4780
43. [43]
  Crupi, V., Majolino, D., Mele, A., Rossi, B., Trotta, F. and Venuti, V., Soft Matter, 2013, 9: 6457
44. [44]
  Tan, S., Blencowe, A., Ladewig, K. and Qiao, G.G., Soft Matter, 2013, 9: 5239
45. [45]
  Gao, M., Toita, S., Sawada, S.I., Akiyoshi, K. and Stokke, B.T., Soft Matter, 2013, 9: 5178
46. [46]
  Wang, Q., Chen, Y. and Liu, Y., Polym. Chem., 2013, 4: 4192
47. [47]
  Feng, C., Lu, G., Li, Y. and Huang, X., Langmuir, 2013, 29: 10922
48. [48]
  Zhang, Q.W., Qu, D., Ma, X. and Tian, H., Chem. Commun., 2013, 49: 9800
49. [49]
  Kang, Y., Yuan, J., Yan, Q., Zheng, L. and Zhou, L., Polym. Adv. Technol., 2012, 23: 255
50. [50]
  Stadermann, J., Komber, H., Erber, M., Dbritz, F., Ritter, H. and Voit, B., Macromolecules, 2011, 44: 3250
51. [51]
  Jin, H., Zheng, Y., Liu, Y., Cheng, H., Zhou, Y. and Yan, D., Angew. Chem. Int. Ed., 2011, 50: 10352
52. [52]
  Yhaya, F., Lim, J., Kim, Y., Liang, M., Gregory, A.M. and Stenzel, M.H., Macromolecules, 2011, 44: 8433
53. [53]
  Paolino, M., Ennen, F., Lamponi, S., Cernescu, M., Voit, B., Cappelli, A., Appelhans, D. and Komber, H., Macromolecules, 2013, 46: 3215
54. [54]
  Zhao, L., Jiang, L., Han, Y., Xian, Z., Huang, J. and Yan, Y., Soft Matter, 2013, 9: 7710
55. [55]
  Yang, L., Gomez-Casado, A., Young, J.F., Nguyen, H.D., Cabanas-Danes, J., Huskens, J., Brunsveld, L. and Jonkheijm, P., J. Am. Chem. Soc., 2012, 134: 19199
56. [56]
  Ren, S., Chen, D. and Jiang, M., J. Polym. Sci., Part A: Polym. Chem., 2009, 47: 4267
57. [57]
  Guo, M., Jiang, M., Pispas, S., Yu, W. and Zhou, C., Macromolecules, 2008, 41: 9744
58. [58]
  Pinson, M.B., Sevick, E.M. and Williams, D.R.M., Macromolecules, 2013, 46: 4191
59. [59]
  Rydzek, G., Garnier, T., Schaaf, P., Voegel, J.C., Senger, B., Frisch, B., Haikel, Y., Petit, C., Schlatter, G., Jierry, L. and Boulmedais, F., Langmuir, 2013, 29: 10776
60. [60]
  Tang, C., Inomata, A., Sakai, Y., Yokoyama, H., Miyoshi, T. and Ito, K., Macromolecules, 2013, 46: 6898
61. [61]
  Yu, L., Li, M., Zhou, X.P. and Li, D., Inorg. Chem., 2013, 52: 10232
62. [62]
  Yu, S., Zhang, Y., Wang, X., Zhen, X., Zhang, Z., Wu, W. and Jiang, X., Angew. Chem. Int. Ed., 2013, 52: 7272
63. [63]
  Kohsaka, Y., Koyama, Y. and Takata, T., Angew. Chem. Int. Ed., 2011, 50: 10417
64. [64]
  Tamura, Ikeda, G., Seo, J.H., Tsuchiya, K., Yajima, H., Sasaki, Y., Akiyoshi, K. and Yui, N., Sci. Rep., 2013, 3: 1
65. [65]
  Wang, Y., Wang, H., Chen, Y., Liu, X., Jin, Q. and Ji, J., Chem. Commun., 2013, 49: 7123
66. [66]
  Zhang, Z.X., Liu, K.L. and Li, J., Angew. Chem. Int. Ed., 2013, 52: 6180
67. [67]
  Peng, L., Wang, H., Zhang, H. and Yuan, J., Prog. Chem., 2013, 25: 1942
68. [68]
  Yan, Q., Feng, A., Zhang, H. and Yuan, J., Polym. Chem., 2013, 4: 1216
69. [69]
  Yan, Q., Xin, Y., Zhou R., Yin, Y. and Yuan, J., Chem. Commun., 2011, 47: 9594
70. [70]
  Yan, Q., Yuan, J., Cai, Z., Xin, Y., Kang, Y. and Yin, Y., J. Am. Chem. Soc., 2010, 132: 9268
71. [71]
  Peng, L., Feng A., Zhang, H., Wang, H., Jian, C., Liu, B., Gao, W. and Yuan, J., Polym. Chem., 2014, 5: 1751
72. [72]
  Feng, A., Yan, Q., Zhang, H., Peng, L. and Yuan, J., Chem. Commun., 2014, 50: 4740
73. [73]
  Wu, J. and Gao, C., Macromolecules, 2010, 43: 7139
74. [74]
  Forney, B.S., Baguenard, C. and Guymon, C.A., Soft Matter, 2013, 9: 7458
75. [75]
  Iwasaki, Y., Sakiyama, M., Fujii, S. and Yusa, S., Chem. Commun., 2013, 49: 7824
76. [76]
  Sun, S., Xu, S., Zhang, W., Wu, P., Zhang, W. and Zhu, X., Polym. Chem., 2013, 4: 5800
77. [77]
  Li, S., Peng, B., Yuan, X. and Zhu, M., Polym. Chem., 2014, 5: 562
78. [78]
  Rotzetter, C., Schumacher, C.M., Bubenhofer, S.B., Grass, R.N., Gerber, L.C., Zeltner, M. and Stark, W.J., Adv. Mater., 2012, 24: 5352
79. [79]
  Klaikherd, A., Nagamani, C. and Thayumanavan, S., J. Am. Chem. Soc., 2009, 131: 4830
80. [80]
  Yan, Q., Yuan, J., Yuan, W., Zhou, M., Yin, Y. and Pan, C., Chem. Commun., 2008, 46: 6188
81. [81]
  Crippa, M., Bianchi, A., Cristofori, D., D'Arienzo, M., Merletti, F., Morazzoni, F., Scotti, R. and Simonutti, R., J. Mater. Chem. C, 2013, 1: 484
82. [82]
  Zhang, Z.X., Liu, X., Xu, F.J., Loh, X.J., Kang, E.T., Neoh, K.G. and Li, J., Macromolecules, 2008, 41: 5967
83. [83]
  Zhang, H.J., Xin, Y., Yan, Q., Zhou, L.L., Peng, L. and Yuan, J.Y., Macromol. Rapid Commun., 2012, 33: 1952
84. [84]
  Moad, G., Rizzardo, E. and Thang, S.H., Aust. J. Chem., 2012, 65: 985

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