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Diels-Alder反应在构建特殊结构高分子中的应用

王志鹏, 袁金颖*   

  1. 清华大学化学系 有机光电子与分子工程教育部重点实验室 北京 100084
  • 收稿日期:2012-05-01 修回日期:2012-06-01 出版日期:2012-12-24 发布日期:2012-12-11
  • 通讯作者: 袁金颖 E-mail:yuanjy@mail.tsinghua.edu.cn
  • 基金资助:

    国家自然科学基金项目(No.21174076, 51073090, 20836004)和国家重点基础研究发展计划(973)项目(No.2009CB930602)资助

Applications of Diels-Alder Reaction in Synthesis of Polymers with Well-Defined Architectures

Wang Zhipeng, Yuan Jinying*   

  1. Key Laboratory of Organic Optoelectronics and Molecular Engineering of the Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China
  • Received:2012-05-01 Revised:2012-06-01 Online:2012-12-24 Published:2012-12-11
Diels-Alder反应是一类高选择性、高产率、高可靠性和环境耐受性的反应。从其发现以来,已广泛应用于有机合成化学,成为click化学中的一种类型。近来,在具有特殊结构的高分子合成中,Diels-Alder反应也由于其广泛的实用性与正交性逐渐成为重要的链接手段之一。本文以各类结构高分子的合成作为分类方法,综述Diels-Alder反应在构建这些高分子中的应用。在此基础上,本文展望了Diels-Alder反应在高分子科学中的一些应用前景。发展方法学、应用于特殊结构聚合物的合成、拓宽功能化是相关研究中的关键性问题。
Diels-Alder reaction is a kind of reaction with high selectivity, high productivity, high reliability and condition tolerability. Ever since its discovery, it has been widely used in the organic synthetic chemistry and become a click chemistry. Recently, the Diels-Alder reaction is also gradually becoming an important linking method in the preparation for polymers with well-defined architectures, due to its broad practicability and orthogonality. Based on the classification of polymer architecture, this paper reviews the applications of Diels-Alder reaction in preparing these polymers. Moreover, the paper gives the outlook for further prospect of Diels-Alder reaction in the polymer science. The relative key questions include methodology developments, application in the preparation of polymers with more specialized architectures, and broadening the functional usages. Contents
1 Introduction
1.1 Diels-Alder reaction
1.2 Characteristics of Diels-Alder reaction
2 Diels-Alder reaction approaches of polymers synthesis
2.1 Diels-Alder stepwise polymerization
2.2 Block copolymers
2.3 Cyclic block copolymers
2.4 Telechelic functional group
2.5 Graft copolymers
2.6 Star polymers
2.7 Hyperbranched polymers
3 Other utilization of Diels-Alder reaction
3.1 Survey as a protection group
3.2 Diels-Alder reaction based on the product of a Diels-Alder reaction (double-Diels-Alder reaction)
3.3 Other special architectural polymers
4 Conclusion and outlook

中图分类号: 

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[1] 魏荣宝(Wei R B), 高等有机化学(Advanced Organic Chemistry), 第一版. 北京: 高等教育出版社(Beijing: High Education Press), 2007. 470-475
[2] 杨哲(Yang Z), 魏宏亮(Wei H L), 楚晖娟(Chu H J), 朱靖(Zhu J), 李志成(Li Z C). 高分子通报(Chinese Polymer Bulletin), 2010, 1: 41-50
[3] Nandivada H, Jiang X W, Lahann J. Adv. Mater., 2007, 19: 2197-2208
[4] Murphy E B, Wudl F. Progress in Polymer Science, 2010, 35: 223-251
[5] 张永敏(Zhang Y M). 物理有机化学(Physical Organic Chemistry), 第二版. 上海: 上海科学技术出版社(Shanghai: Shanghai Scientific Technology Press), 2011. 346-353
[6] McElhanon J R, Wheeler D R. Org. Lett., 2001, 3: 2681-2683
[7] Vogt P F, Millere M J. Tetrahedron, 1998, 54: 1317-1348
[8] 潘祖仁(Pan Z R). 高分子化学(增强版)(Polymer Chemistry), 第一版. 北京: 化学工业出版社(Beijing: Chemical Industry Press), 2010. 20
[9] Grigoras M, Sava M, Colotin G, Simionescu C I. Journal of Applied Polymer Science, 2008, 107: 846-853
[10] Grigoras M, Colotin G, Antonoaia N C. Polym, Int., 2004, 53: 1321-1326
[11] Sinnwell S, Inglis A J, Stenzel M H, Barner-Kowollik C. Macromol. Rapid Commun., 2008, 29: 1090-1096
[12] Glassner M, Oehlenschlaeger K K, Gruendling T, Barner-Kowollik C. Macromolecules, 2011, 44: 4681-4689
[13] Durmaz H, Sanyal A, Hizal G, Tunca U. Polym. Chem., 2012, 3: 825-835
[14] Mcelhanon J R, Russick E M, Wheeler D R, Loy D A, Aubert J H. Journal of Applied Polymer Science, 2002, 85: 1496-1502
[15] Dag A, Durmaz H, Demir E, Hizal G, Tunca U. Journal of Polymer Science Part A: Polymer Chemistry, 2008, 46: 6969-6977
[16] Tasdelen M A. Polym. Chem., 2011, 2: 2133-2145
[17] Wei H L, Yang Z, Chen Y, Chu H J, Zhu J, Li Z C. European Polymer Journal, 2010, 46: 1032-1039
[18] Cho M J, Choi D H, Sullivan P A, Akelaitis A J P, Dalton L R. Progress in Polymer Science, 2008, 33: 1013-1058
[19] Gunay U S, Durmaz H, Gungor E, Dag A, Hizal G, Tunca U. Journal of Polymer Science Part A: Polymer Chemistry, 2012, 50: 729-735
[20] Dag A, Durmaz H, Hizal G, Tunca U. Journal of Polymer Science Part A: Polymer Chemistry, 2008, 46: 302-313
[21] Altintas O, Yankul B, Hizal G, Tunca U. Journal of Polymer Science Part A: Polymer Chemistry, 2007, 45: 3588-3598
[22] Altintas O, Hizal G, Tunca U. Journal of Polymer Science Part A: Polymer Chemistry, 2008, 46: 1218-1228
[23] Durmaz H, Karatas F, Tunca U, Hizal G. Journal of Polymer Science Part A: Polymer Chemistry, 2006, 44: 3947-3957
[24] Dag A, Durmaz H, Tunca U, Hizal G. Journal of Polymer Science Part A: Polymer Chemistry, 2009, 47: 178-187
[25] Gozgen A, Dag A, Durmaz H, Sirkecioglu O, Hizal G, Tunca U. Journal of Polymer Science Part A: Polymer Chemistry, 2009, 47: 497-504
[26] Durmaz H, Dag A, Hizal A, Hizal G, Tunca U. Journal of Polymer Science Part A: Polymer Chemistry, 2008, 46: 7091-7100
[27] Durmaz H, Dag A, Gursoy D, Demirel A L, Hizal G, Tunca U. Journal of Polymer Science Part A: Polymer Chemistry, 2010, 48: 1557-1564
[28] Durmaz H, Dag A, Erdogan E, Demirel A L, Hizal G, Tunca U. Journal of Polymer Science Part A: Polymer Chemistry, 2010, 48: 99-108
[29] Gungor E, Cote G, Erdogan T, Durmaz H, Demirel A L, Hizal G, Tunca U. Journal of Polymer Science Part A: Polymer Chemistry, 2007, 45: 1055-1065
[30] Morgenroth F, Reuther E, Müllen K. Angew. Chem. Int. Ed., 1997, 36: 631-634
[31] Franc G, Kakkar A K. Chem. Eur. J., 2009, 15: 5630-5639
[32] McElhanon J R, Wheeler D R. Org. Lett., 2001, 3: 2681-2683
[33] Szalai M L, McGrath D V, Wheeler D R, Zifer T, McElhanon J R. Macromolcules, 2007, 40: 818-823
[34] Durmaz H, Colakoglu B, Tunca U, Hizal G. Journal of Polymer Science Part A: Polymer Chemistry, 2006, 44: 1667-1675
[35] Mantovani G, Lecolley F, Tao L, Haddleton D M, Clerx J, Cornelissen J J L M, Velonia K. J. Am. Chem. Soc., 2005, 127: 2966-2973
[36] Wiggins K M, Syrett J A, Haddleton D M, Bielawski C W. J. Am. Chem. Soc., 2011, 133: 7180-7189
[37] Binder W H, Sachsenhofer R. Macromol. Rapid Commun., 2007, 28: 15-54
[38] Giacalone F, Martin N. Chem. Rev., 2006, 106: 5136-5190
[39] Zydziak N, Hübner C, Bruns M, Barner-Kowollik C. Macromolecules, 2011, 44: 3374-3380
[40] Sarkar S, Bekyarova E, Haddon R C. Accounts of Chemical Research, 2012, 45: 673-682
[41] Sarkar S, Bekyarova E, Niyogi S, Haddon R C. J. Am. Chem. Soc., 2011, 133: 3324-3327
[42] Murphy E B, Wudl F. Progress in Polymer Science, 2010, 35: 223-251
[43] Liu X F, Liu H B, Zhou W D, Zheng H Y, Yin X D, Li Y L, Guo Y B, Zhu M, Ouyang C B, Zhu D B, Xia A D. Langmuir, 2010, 26: 3179-3185
[44] Yoshizawa M, Tamura M, Fujita M. Science, 2006, 312: 251-254
[45] Adzima B J, Kloxin C J, Bowman C N. Adv. Mater., 2010, 22: 2784-2787
[46] Kloxin C J, Scott T F, Adzima B J, Bowman C N. Macromolecules, 2010, 43: 2643-2653
[47] Luo J D, Huang S, Cheng Y J, Kim T D, Shi Z W, Zhou X H, Jen A K Y. Org. Lett., 2007, 9: 4471-4474
[48] Sumerlin B S, Vogt A P. Macromolecules, 2010, 43: 1-13
[49] Goldmann A S, Tischer T, Barner L, Bruns M, Barner-Kowollik C. Biomacromolecules, 2011, 12: 1137-1145
[50] 闫强(Yan Q), 袁金颖(Yuan J Y), 康燕(Kang Y), 袁伟忠(Yuan W Z). 化学进展(Progress in Chemistry), 2008, 20: 1972-1979
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