基于点击化学合成含有全氟环丁基芳基醚的ABA三嵌段共聚物
收稿日期: 2013-05-26
修回日期: 2013-06-19
网络出版日期: 2013-07-03
基金资助
国防科大校预研(No. JC11-02-15)资助项目
Synthesis of Perfluorocyclobutyl Aryl Ether-Containing ABA Triblock Copolymer via Click Chemistry
Received date: 2013-05-26
Revised date: 2013-06-19
Online published: 2013-07-03
Supported by
Project supported by the Advanced Research Project of National University of Defense Technology (No. JC11-02-15).
由于三氟乙烯基芳基醚单体独特的聚合机理和反应温度, 因此难以通过顺序投料法来合成含有全氟环丁基芳基醚结构的嵌段共聚物. 我们通过端基修饰的方法在全氟环丁基芳基醚聚合物链端引入叠氮基团, 通过点击化学与含有炔基的聚乙二醇相连, 制备了含有全氟环丁基芳基醚的ABA三嵌段共聚物.
关键词： 嵌段共聚物; 端基偶联法; 点击化学; 全氟环丁基芳基醚聚合物
李炳臻 , 李义和 . 基于点击化学合成含有全氟环丁基芳基醚的ABA三嵌段共聚物[J]. 有机化学, 2013 , 33(10) : 2148 -2154 . DOI: 10.6023/cjoc201305041
Because of the unusual polymerization mechanism and normal high polymerization temperature of trifluorovinyl aryl ether monomers, it is difficult to synthesize perfluorocyclobutyl aryl ether (PFCB)-containing block copolymer via sequential addition of monomers. Here a coupling reaction via click chemistry to prepare PFCB-containing ABA triblock copolymer is reported. An azide-ended PFCB polymer, which was firstly prepared by end-modification of methyl-ended PFCB polymer, was coupled with alkynyl-ended polyethylene glycol via the azide alkyne Huisgen cycloaddition.
[1] Kim, H. C.; Park, S. M.; Hinsberg, W. D. Chem. Rev. 2012, 110, 146.
[2] (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312.
(b) Shen, H.; Eisenberg, A. Macromolecules 2000, 33, 2561.
[3] (a) Harada, A.; Kataoka, K. Macromolecules 1995, 28, 5294.
(b) Meier, W. Chem. Soc. Rev. 2000, 29, 295.
(c) Kim, S. Y.; Ha, J. C.; Lee, Y. M. J. Controlled Release 2000, 65, 345.
(d) Moffitt, M,; Eisenberg, A. Macromolecules 1997, 30, 4363.
[4] Hadjichristidis, N.; Pitsikalis, M.; Iatrou, H. In Block Copolymers I, Ed.: Abetz, V., Springer, Berlin, 2005, pp 1～124.
[5] Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
[6] Tsarevsky, N. V.; Sumerlin, B. S.; Matyjaszewski, K. Macromolecules 2005, 38, 3558.
[7] Gao, H.; Matyjaszewski, K. Macromolecules 2006, 39, 4960.
[8] Laurent, B. A.; Grayson, S. M. J. Am. Chem. Soc. 2006, 128, 4238.
[9] Xiong, X. Q. Chin. J. Org. Chem. 2010, 30, 307 (in Chinese). (熊兴泉, 有机化学, 2010, 30, 307.)
[10] Kong, L. Z.; Qiao, H. M.; Jiang, B. B. Acta Chim. Sinica 2011, 69, 1817 (in Chinese). (孔立智, 乔华明, 蒋必彪, 化学学报, 2011, 69, 1817.)
[11] Zhang, S. H.; Zhu, H. W.; Zhang, M. Z.; Ni, P. H. Acta Chim. Sinica 2011, 69, 2166 (in Chinese). (张世华, 朱汇雯, 张明祖, 倪沛红, 化学学报, 2011, 69, 2166.)
[12] O'Reilly, R. K.; Joralemon, M. J.; Hawker, C. J.; Wooley, K. L. Chem. Eur. J. 2006, 12, 6776.
[13] Babb, D. A.; Ezzell, B. R.; Clement, K. S.; Richey, W. F.; Kennedy, A. P. J. Polym. Sci.: Part A: Polym. Chem. 1993, 31, 3465.
[14] Babb, D. A. In Fluoropolymers 1 Synthesis, Eds.: Hougham, G.; Cassidy, P. E.; Johns, K.; Davidson, T., Kluwer Academic Publishers, New York, 1999.
[15] (a) Huang, X. Y.; Lu, G. L.; Peng, D.; Zhang, S.; Qing, F. L. Macromolecules 2005, 38, 7299.
(b) Lu, G. L.; Zhang, S.; Huang, X. Y. J. Polym. Sci.: Part A: Polym. Chem. 2006, 44, 5438.
(c) Lu, G. L.; Zhang, S.; Li, Y. J.; Huang, X. Y. Chin. J. Chem. 2011, 29, 2791.
[16] (a) Kennedy, A. P.; Babb, D. A.; Bremmer, J. N.; Pasztor, A. J. Jr. J. Polym. Sci., Part A: Polym. Chem. 1995, 33, 1859.
(b) Li, Y. J.; Zhang, S.; Feng, C.; Zhang, Y. Q.; Li, Q. N.; Li, W. X.; Huang, X. Y. Chin. J. Chem. 2009, 27, 2261.
[17] (a) Liu, H.; Li, Y. J.; Zhang, S.; Yang, D.; Hu, J. H.; Huang, X. Y. J. Polym. Sci.: Part A: Polym. Chem. 2011, 49, 11.
(b) Liu, H.; Zhang, S.; Li, Y. J.; Yang, D.; Hu, J. H.; Lu, G. L.; Huang, X. Y. Polymer 2010, 51, 5198.
[18] Wang, X. H.; Feng, Z. G. Acta Polym. Sin. 2000, 3, 350.
[19] Gao, H. F.; Louche, G.; Sumerlin, B. S.; Jahed, N.; Golas, P.; Matyjaszewski, K. Macromolecules 2005, 38, 8979.
[20] Smith, D. W.; Babb, D. A. Macromolecules 1996, 29, 852.
[21] Kastsuhara, Y.; DesMarteau, D. D. J. Am. Chem. Soc. 1980, 102, 2681.
/
| 〈 |
|
〉 |
