Recent Progress of Organocatalyzed Group Transfer Polymerization

doi:10.6023/A20040115

Acta Chimica Sinica ›› 2020, Vol. 78 ›› Issue (8): 733-745.DOI: 10.6023/A20040115 Previous Articles Next Articles

Review

有机催化基团转移聚合的研究进展

陈友根, 丁远生

深圳大学高等研究院深圳 518060

投稿日期:2020-04-24 发布日期:2020-06-15
通讯作者: 陈友根 E-mail:chenyg@szu.edu.cn
作者简介:陈友根,深圳大学高等研究院研究员,北海道大学特聘教员,于2012年9月获得日本北海道大学博士学位,并在博士期间兼任日本学术振兴会(JSPS)特别研究员.同年至2013年于苏黎世联邦理工学院(ETH Zurich)从事博士后工作.2013年至2015年于北海道大学工学研究院担任助理教授,于2016年始在深圳大学高等研究院任独立研究员并兼职北海道大学特聘教员.主要从事聚合物的可控合成,聚合物结构-性能关系的解析,以及新型聚合方法的开发.近年来主要关注于应用有机小分子催化剂合成无金属残留的绿色聚合物材料,以实现所得高分子在光电、生物以及环境友好型材料等领域的应用.除此之外,也关注各种对温度、手性等外部刺激产生高敏性感应的高分子材料的开发与应用.近年来在高分子化学领域重要国际刊物发表高水平论文50余篇,发表著作章节1章.
丁远生,深圳大学高等研究院硕士研究生,于2018年6月从深圳大学高等研究院化学专业毕业,2018年6月进入高分子化学课题组开始硕士研究生阶段学习,已发表论文两篇.
基金资助:
项目受国家自然科学基金（No.21604057）、深圳市海外高层次人才启动经费（No.000215）和深圳市科技研发资金（No.JCYJ20190808154011907）资助.

Recent Progress of Organocatalyzed Group Transfer Polymerization

Chen Yougen, Ding Yuansheng

Institute for Advanced Study, Shenzhen University, Shenzhen 518060

Received:2020-04-24 Published:2020-06-15
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21604057), Natural Science Foundation of SZU (No. 000215), Shenzhen Science and Technology Research Grant (No. JCYJ20190808154011907).

Group transfer polymerization (GTP) is a living polymerization method for acrylic-derived monomers developed by DuPont after living anionic polymerization in the 1980s. The acrylic-derived monomers mainly include acrylate, methacrylate, acrylamide and acrylonitrile. The elementary initiation and propagation reactions in GTP are all rooted in the Mukaiyama-Michael addition reaction. Therefore, in principle both base and acid can sever as the catalyst for GTP. Before the small molecular organocatalyst is applied to the polymerization method, the normally used base has been a soluble ionic compound containing a sterically hindered cation, in which the nucleophilic anion acts as the true catalyst. The normally used acid has been a metal or transition metal compound having Lewis acidity. Since 2007, small organic bases and acids have been gradually used to catalyze GTP, and this type of polymerization has been named as organocatalyzed GTP. Compared with the conventional one, organocatalyzed GTP has made a great improvement in the aspects of molecular weight and molecular weight distribution control of acrylic polymers, scope of polymerizable monomers, topological design of polymer, etc. This review mainly focuses on the author's recent work and will be discussed from four aspects: GTP using organic strong base, GTP using organic strong acid, a novel hydrosilane-based GTP, and polymerization mechanism.

Key words: organocatalysis, group transfer polymerization, polymerizable monomer, molecular weight and molecular weight distribution, polymer topology

Cite this article

Chen Yougen, Ding Yuansheng. Recent Progress of Organocatalyzed Group Transfer Polymerization[J]. Acta Chimica Sinica, 2020, 78(8): 733-745.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
[2] MacMillan, D. W. C. Nature 2008, 455, 304.
[3] Xiao, Y.; Wang, Y.; Zhou, Z. Chinese J. Org. Chem. 2019, 39, 2203.
[4] Wang, L.; Lin, G.; Zhao, M.; Liu, D.; Jin, Y. Chinese J. Org. Chem. 2018, 38, 642 (in Chinese). (王黎明, 林赓, 赵美君, 刘东垚, 金瑛, 有机化学, 2018, 38, 642.)
[5] Ma, S.; Zhong, Y.; Wang, S.; Xu, Z.; Chang, M.; Wang, R. Acta Chim. Sinica 2014, 72, 825 (in Chinese). (马世雄, 钟源, 王守磊, 许兆青, 常民, 王锐, 化学学报, 2014, 72, 825.)
[6] Zhao, H.; Meng, W.; Yang, Z.; Tian, T.; Sheng, Z.; Li, H.; Song, X.; Zhang, Y.; Yang, S.; Li, B. Chinese J. Chem. 2014, 32, 417.
[7] Nederberg, F.; Connor, E. F.; Möller, F.; Glauser, M. T.; Hedrick, J. L. Angew. Chem. Int. Ed. 2001, 40, 2712.
[8] Misaka, H.; Kakuchi, R.; Zhang, C. H.; Sakai, R.; Satoh, T.; Kakuchi, T. Macromolecules 2009, 42, 5091.
[9] Dove, A. P.; Pratt, R. C.; Lohmeijer, B. G. G.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2005, 127, 13798.
[10] Miyake, G. M.; Chen, E. Y.-X. Macromolecules 2011, 44, 4116.
[11] Sanda, F.; Sanada, H.; Shibasaki, Y.; Endo, T. Macromolecules 2002, 35, 680.
[12] Persson, P. V.; Schroder, J.; Wickholm, K.; Hedenstrom, E.; Iversen, T. Macromolecules 2004, 37, 5889.
[13] Oledzka, E.; Narine, S. S. J. Appl. Polym. Sci. 2011, 119, 1873.
[14] Makiguchi, K.; Satoh, T.; Kakuchi, T. Macromolecules 2011, 44, 1999.
[15] Gazeau-Bureau, S.; Delcroix, D.; Martin-Vaca, B.; Bonrissou, D.; Navarro, C.; Magnet, S. Macromolecules 2008, 41, 3782.
[16] Bourissou, D.; Martin-Vaca, B.; Dumitrescu, A.; Graullier, M.; Lacombe, F. Macromolecules 2005, 38, 9993.
[17] Kadota, J.; Pavlović, D.; Desvergne, J.; Bibal, B.; Peruch, F.; Deffieux, A. Macromolecules 2010, 43, 8874.
[18] Helou, M.; Miserque, O.; Brusson, J.; Carpentier, J.; Guillaume, S. M. Chem. Eur. J. 2010, 16, 13805.
[19] Connor, E. F.; Nyce, G. W.; Myers, M.; Mock, A.; Hedrick, J. L. J. Am. Chem. Soc. 2002, 124, 914.
[20] Nyce, G. W.; Glauser, T.; Connor, E. F.; Mock, A.; Waymouth, R. M.; Hedrick. J. L. J. Am. Chem. Soc. 2003, 125, 3046.
[21] Coulembier, O.; Dove, A. P.; Pratt, R. C.; Sentman, A. C.; Culkin, D. A.; Mespouille, L.; Dubois, P.; Waymouth, R. M.; Hedrick, J. L. Angew. Chem. Int. Ed. 2005, 44, 4964.
[22] Csihony, S.; Culkin, D. A.; Sentman, A. C.; Dove, A. P.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2005, 127, 9079.
[23] Zhang, L.; Nederberg, F.; Pratt, R. C.; Waymouth, R. M.; Hedrick, J. L.; Wade, C. G. Macromolecules 2007, 40, 4154.
[24] Nederberg, F.; Lohmeijer, B. G. G.; Leibfarth, F.; Pratt, R. C.; Choi, J.; Dove, A. P.; Waymouth, R. M.; Hedrick, J. L. Biomacromolecules 2007, 8, 153.
[25] Lohmeijer, B. G. G.; Dubois, G.; Leibfarth, F.; Pratt, R. C.; Nederberg, F.; Nelson, A.; Waymouth, R. M.; Wade, C. G.; Hedrick, J. L. Org. Lett. 2006, 8, 4683.
[26] Zhang, L.; Nederberg, F.; Pratt, R. C.; Waymouth, R. M.; Hedrick, J. L.; Wade, C. G. Macromolecules 2007, 40, 4154.
[27] Zhang, L.; Nederberg, F.; Messman, J. M.; Pratt, R. C.; Hedrick, J. L.; Wade, C. G. J. Am. Chem. Soc. 2007, 129, 12610.
[28] Webster, O. W.; Hertler, W. R.; Sogah, D. Y.; Farnham, W. B.; RajanBabu, T. V. J. Am. Chem. Soc. 1983, 105, 5706.
[29] Webster, O. W. Adv. Polym. Sci. 2004, 167, 1.
[30] Schubert, W.; Bandermann, F. Makromol. Chem. 1989, 190, 2161.
[31] Schubert, W.; Sitz, H. D.; Bandermann, F. Makromol. Chem. 1989, 190, 2193.
[32] Sogah, D. Y.; Hertler, W. R.; Webster, O. W.; Cohen, G. M. Macromolecules 1987, 20, 1473.
[33] Schubert, W.; Bandermann, F. Makromol. Chem. 1989, 190, 2721.
[34] Hertler, W. R.; Sogah, D. Y.; Webster, O. W. Macromolecules 1984, 17, 1415.
[35] Hellstern, A. M.; DeSimone, J. M.; McGrath, J. E. Polym. Prepr. 1988, 29, 342.
[36] Dicker, I. B.; Cohen, G. M.; Farnham, W. B.; Hertler, W. R.; Laganis, E. D.; Sogah, D. Y. Macromolecules 1990, 23, 4034.
[37] Patrickios, C. S.; Hertler, W. R.; Abbott, N. L.; Hatton, T. A. Macromolecules 1994, 27, 930.
[38] Eggert, M.; Freitag, R. J. Polym. Sci. Part A: Polym. Chem. 1994, 32, 803.
[39] Ute, K.; Tarao, T.; Hongo, S.; Ohnuma, K.; Hatada, K.; Kitayama, T. Polym. J. 1999, 31, 177.
[40] Ute, K.; Ohnuma, H.; Shimizu, I.; Kitayama, T. Polym. J. 2006, 38, 999.
[41] Dicker, I. B. Polym. Prepr. 1988, 29, 114.
[42] Zhuang, R.; Müller, A. H. E. Macromol. Symp. 1994, 85, 379.
[43] Zhuang, R.; Müller, A. H. E. Macromolecules 1995, 28, 8035.
[44] Zhuang, R.; Müller, A. H. E. Macromolecules 1995, 28, 8043.
[45] Ute, K.; Tarao, T.; Hatada, K. Polymer 1997, 44, 7869.
[46] Ute, K.; Tarao, T.; Kitayama, T. Polym. J. 2005, 37, 578.
[47] White, D.; Matyjaszewski, K. Polym. Prepr. 1995, 36, 286.
[48] Fuchise, K.; Chen, Y.-G.; Satoh, T.; Kakuchi, T. Polym. Chem. 2013, 4, 4278.
[49] Raynaud, J.; Ciolino, A.; Baceiredo, A.; Destarac, M.; Bonnette, F.; Kato, T.; Gnanou, Y.; Taton, D. Angew. Chem. Int. Ed. 2008, 47, 5390.
[50] Scholten, M. D.; Hedrick, J. L.; Waymouth, R. M. Macromolecules 2008, 41, 7399.
[51] Raynaud, J.; Liu, N.; Gnanou, Y.; Taton, D. Macromolecules 2010, 43, 8853.
[52] Raynaud, J.; Liu, N.; Fèvre, M.; Gnanou, Y.; Taton, D. Polym. Chem. 2011, 2, 1706.
[53] Scholten, M. D.; Hedrick, J. L.; Waymouth, R. M. Polym. Prepr. 2007, 48, 167.
[54] Raynaud, J.; Gnanou, Y.; Taton, D. Macromolecules 2009, 42, 5996.
[55] Raynaud, J.; Gnanou, Y.; Taton, D. PMSE Prepr. 2009, 101, 1771.
[56] Zhang, Y.; Chen, E. Y.-X. Angew. Chem. Int. Ed. 2012, 51, 2465.
[57] Fèvre, M.; Vignolle, J.; Heroguez, V.; Taton, D. Macromolecules 2012, 45, 7711.
[58] Zhang, Y.; Chen, E. Y.-X. Macromolecules 2008, 41, 36.
[59] Zhang, Y.; Chen, E. Y.-X. Macromolecules 2008, 41, 6353.
[60] Miyake, G. M.; Zhang, Y.; Chen, E. Y.-X. Macromolecules 2010, 43, 4902.
[61] Zhang, Y.; Gustafson, O.; Chen, E. Y-X. J. Am. Chem. Soc. 2011, 133, 13674.
[62] Chen, E. Y.-X. Chem. Rev. 2009, 109, 5157.
[63] Zhang, Y.; Lay, F.; García-García, P.; List, B. Chem. Eur. J. 2010, 16, 10462.
[64] Kakuchi, T.; Chen, Y.-G.; Kitakado, J.; Mori, K.; Fuchise, K.; Satoh, T. Macromolecules 2011, 44, 4641.
[65] Chen, Y.-G.; Takada, K.; Kubota, N.; Eric, O.-T.; Ito, T.; Isono, T.; Satoh, T.; Kakuchi, T. Polym. Chem. 2015, 6, 1830.
[66] Eric, O.-T.; Chen, Y.-G.; Takada, K.; Sato, S.; Satoh, T.; Kakuchi, T. Polym. Chem. 2015, 6, 7841.
[67] Chen, Y.-G.; Fuchise, K.; Kawaguchi, S.; Satoh, T.; Kakuchi, T. Macromolecules 2011, 44, 9091.
[68] Hsu, J.-C.; Chen, Y.-G.; Kakuchi, T.; Chen, W.-C. Macromolecules 2011, 44, 5168.
[69] Kikuchi, S.; Chen, Y.-G.; Fuchise, K.; Takada, K.; Kitakado, J.; Sato, S.; Satoh, T.; Kakuchi, T. Polym. Chem. 2014, 5, 4701.
[70] Kakuchi, R.; Chiba, K.; Fuchise, K.; Sakai, R.; Satoh, T.; Kakuchi, T. Macromolecules 2009, 42, 8747.
[71] Chen, Y.-G.; Takada, K.; Fuchise, K.; Satoh, T.; Kakuchi, T. J. Polym. Sci. Part A: Polym. Chem. 2012, 50, 3277.
[72] Takada, K.; Fuchise, K.; Chen, Y.-G.; Satoh, T.; Kakuchi, T. J. Polym. Sci. Part A: Polym. Chem. 2012, 50, 3560.
[73] Takada, K.; Ito, T.; Kitano, K.; Tuschida, S.; Takagi, Y.; Chen, Y.-G.; Satoh, T.; Kakuchi, T. Macromolecules 2015, 48, 511.
[74] Takada, K.; Fuchise, K.; Kubota, N.; Ito, T.; Chen, Y.-G.; Satoh, T.; Kakuchi, T. Macromolecules 2014, 47, 5514.
[75] Fuchise, K.; Sakai, R.; Satoh, T.; Sato, S.; Narumi, A.; Kawaguchi, S.; Kakuchi, T. Macromolecules 2010, 43, 5589.
[76] Fuchise, K.; Chen, Y.-G.; Takada, K.; Satoh, T.; Kakuchi, T. Macromol. Chem. Phys. 2012, 213, 1604.
[77] Kikuchi, S.; Chen, Y.-G.; Kitano, K.; Takada, K.; Satoh, T.; Kakuchi, T. Polym. Chem. 2015, 6, 6845.
[78] Kikuchi, S.; Chen, Y.-G.; Ichinohe, E.; Sato, S.; Duan, Q.; Shen, X.-D.; Kakuchi, T. Macromolecules 2016, 49, 4828.
[79] Fuchise, K.; Tsuchida, S.; Takada, K.; Chen, Y.-G.; Satoh, T.; Kakuchi, T. ACS Macro. Lett. 2014, 3, 1015.
[80] Chen, Y.-G.; Kitano, K.; Tsuchida, S.; Kikuchi, S.; Takada, K.; Satoh, T.; Kakuchi, T. Polym. Chem. 2015, 6, 3502.
[81] Kikuchi, S.; Chen, Y.-G.; Kitano, K.; Satoh, T.; Kakuchi, T. Macromolecules 2016, 49, 3049.
[82] Chen, Y.-G.; Jia, Q.; Ding, Y.,; Sato, S.; Xu, L.; Zang, C.;, Shen, X.; Kakuchi, T. Macromolecules 2019, 52, 844.
[83] Chen Y.-G.; Kakuchi, T. Chem. Rec. 2016, 16, 2161.
[84] Chen, Y.-G.; Shen, X.-D.; Kakuchi, T. Journal of The Adhesion Society of Japan, 2017, 53, 432. (陳友根, 沈賢徳, 覚知豊次, 日本接着学会誌, 2017, 53, 432.)
[85] Chen, Y.-G.; Fuchise, K.; Satoh, T.; Kakuchi, T. In Anionic Polymerization: Principles, Practice, Strength, Consequences, and Applications, Springer, Tokyo, 2015, pp. 451～494.

有机催化基团转移聚合的研究进展

Recent Progress of Organocatalyzed Group Transfer Polymerization

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 9

Recommended Articles

Metrics

Comments

[1]	Xiaochen Wang, Zeyao Ji, Jian Liu, Bingfu Wang, Hui Jin, Lixin Zhang. Advances in Organocatalytic Asymmetric Reactions Involving Thioesters [J]. Acta Chimica Sinica, 2023, 81(1): 64-83.
[2]	Lu Hong, Liu Jin-Yu, Li Hong-Yu, Xu Peng-Fei. Recent Developments in N-Heterocyclic Carbene and Transition-Metal Cooperative Catalysis [J]. Acta Chim. Sinica, 2018, 76(11): 831-837.
[3]	Zhang Mao-Mao, Luo Yuan-Yuan, Lu Liang-Qiu, Xiao Wen-Jing. Advances on Asymmetric Allylic Substitutions under Synergetic Catalysis System with Transition Metals and Organocatalysts [J]. Acta Chim. Sinica, 2018, 76(11): 838-849.
[4]	Shi Minglin, Zhan Gu, Du Wei, Chen Yingchun. Direct Asymmetric Aza-Vinylogous Mannich Reaction of Nitrones from Isatins and Ketimines [J]. Acta Chim. Sinica, 2017, 75(10): 998-1002.
[5]	Zhang Qichao, Lü Jian, Luo Sanzhong. Carbocation Lewis Acid Catalyzed Redox-Neutral α-C(sp³)H Arylation of Amines [J]. Acta Chim. Sinica, 2016, 74(1): 61-66.
[6]	Yu Tianyang, Wang Yao, Xu Pengfei. A New Approach for Supramolecular Iminium Catalysis [J]. Acta Chimica Sinica, 2014, 72(7): 845-848.
[7]	Wang Yuhui, Cao Zhongyan, Niu Yanfei, Zhao Xiaoli, Zhou Jian. Highly Enantioselective Organocatalytic aza-Henry Reaction of Nitroalkanes to N-Boc Isatin Ketimines [J]. Acta Chimica Sinica, 2014, 72(7): 867-872.
[8]	Ma Shixiong, Zhong Yuan, Wang Shoulei, Xu Zhaoqing, Chang Min, Wang Rui. Organocatalyzed Asymmetric Allylic Alkylation of MBH-Carbonates with Pyrazolones [J]. Acta Chimica Sinica, 2014, 72(7): 825-829.
[9]	Sun Xunhao, Peng Jing, Zhang Shuyang, Zhou Qingqing, Dong Lin, Chen Yingchun. Asymmetric Allylic Alkylation of Cyclic N-Sulfonylimines with Morita-Baylis-Hillman Carbonates of Isatins [J]. Acta Chimica Sinica, 2012, 70(16): 1682-1685.