Recent Advances in Fluorine-containing Materials with Extreme Environment Resistance

doi:10.6023/A18080340

Acta Chim. Sinica ›› 2018, Vol. 76 ›› Issue (10): 739-748.DOI: 10.6023/A18080340 Previous Articles Next Articles

Review

耐极端条件含氟材料的研究进展

金维则, 陆国林, 李永军, 黄晓宇

中国科学院上海有机化学研究所上海 200032

投稿日期:2018-08-17 发布日期:2018-09-12
通讯作者: 黄晓宇 E-mail:xyhuang@sioc.ac.cn
作者简介:金维则,中国科学院上海有机化学研究所助理研究员,2015年于The University of Akron取得高分子工程硕士学位.主要从事功能高分子材料的研究.;陆国林,中国科学院上海有机化学研究所副研究员,2013年入选中国科学院青年创新促进会.目前主要从事接枝共聚物、刺激响应性聚合物和高性能含氟聚合物的研究.已主持完成了国家自然科学基金青年基金(20904065)和面上项目(21174158)各1项,目前主持国家自然科学基金面上项目"主链含有氟甲基/三氟甲硫基的聚丙烯酸酯类共聚物的构建"(21674124).作为第一作者或通讯作者,已在Polym.Chem.,J.Polym.Sci.Polym.Chem.和Polymer等国际学术期刊上发表SCI论文20多篇.
基金资助:
项目受国家重大科学研究计划项目（No.2015CB931900），国家杰出青年科学基金（No.51825304），国家自然科学基金重点项目（No.21632009），国家自然科学基金面上项目（Nos.21674124，51773222和51773223），中国科学院战略性科技先导专项（B类）（No.XDB20000000），上海市基础研究重大项目（No.18JC1410600）及上海市科技创新项目（No.17DZ1205400）资助.

Recent Advances in Fluorine-containing Materials with Extreme Environment Resistance

Jin Weize, Lu Guolin, Li Yongjun, Huang Xiaoyu

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2018-08-17 Published:2018-09-12
Contact: 10.6023/A18080340 E-mail:xyhuang@sioc.ac.cn
Supported by:
Project supported by the National Major Scientific Research Project (No. 2015CB931900), the National Science Fund for Distinguished Young Scholars (No. 51825304), the National Major Natural Science Foundation Project (No. 21632009), National Natural Science Foundation Project (Nos. 21674124, 51773222, 51773223), Special Science and Technology Pilot Program of Chinese Academy of Sciences (Class B) (No. XDB20000000), Shanghai Major Basic Research Project (No. 18JC1410600) and Shanghai Scientific and Technological Innovation Project (No. 17DZ1205400).

The extreme environment resistance materials can be normally used under severe conditions (e.g. T ≤ -50℃ or T ≥ 200℃, 1000 h exposed to UV light etc.), which common hydrocarbon materials cannot tolerate. It was found that fluorine atoms can effectively enhance the extreme environment resistance property of materials. The reason why fluorine atoms have such ability is mainly due to two key factors:first, fluorine and carbon elements are in the same cycle of the periodic table, the electronegativity of fluorine is large (4.0) and its atomic radius is small; second, polarization of fluorine atom is extremely low. The C-F bond is the strongest chemical single bond (≥ 116 kcal/mol) in which the carbon atom participates. It is a short bond and highly polarized. This paper makes brief introduction to the development and present situation of fluorine-containing materials with extreme environment resistance. In the field of fluorination methods, the history of fluorine chemistry since 1970s, the researches on the formation and fracture of carbon-fluorine bond, the influence of fluorine on the formation of carbon-carbon bond and the related researches on polyfluoro-arylation methods are introduced. This paper also introduces the important results of fluorine-containing materials in lithium isotope extraction, thermo-stable fluoropolymers which can be applied in aviation, aerospace, automobile and other fields, as well as the preparation of high-performance fluorine-containing materials with low dielectric constant in electronic equipment and communication fields. In the future, how to further develop and optimize the fluorine-containing materials with extreme environment resistance and put the research results into large-scale use is the working direction for researchers.

Key words: extreme environment resistance, fluorine-containing material, nanomaterial, polymer, synthesis

Cite this article

Jin Weize, Lu Guolin, Li Yongjun, Huang Xiaoyu. Recent Advances in Fluorine-containing Materials with Extreme Environment Resistance[J]. Acta Chim. Sinica, 2018, 76(10): 739-748.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Bai, C. L.; Liu, M. H. Angew. Chem., Int. Ed. 2013, 52, 2678.
[2] Hiyama, T.; Kanie, K.; Kusumoto, T.; Morizawa, Y.; Shimizu, M. Organofluorine Compounds:Chemistry and Applications, Springer, New York, 2000, pp. 1~272.
[3] Uneyama, K. Organofluorine Chemistry, Blackwell, Oxford, 2006, pp. 1~337.
[4] Sharpless, K. B. Efficient Preparations of Fluorine Compounds, Wiley, Hoboken, 2013, pp. I~XI.
[5] Shibata, N.; Matsnev, A.; Cahard, D. Beilstein J. Org. Chem. 2010, 6, 65.
[6] Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. 2000, 39, 4359.
[7] Chen, Q. Y.; Duan, J. X. Tetrahedron Lett. 1993, 34, 4241.
[8] Su, D. B.; Duan, J. X.; Chen, Q. Y. Tetrahedron Lett. 1991, 32, 7689.
[9] Grushin, V. V. Acc. Chem. Res. 2010, 43, 160.
[10] Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679.
[11] Wang, X. S.; Mei, T. S.; Yu, J. Q. J. Am. Chem. Soc. 2009, 131, 7520.
[12] Hull, K. L.; Anani, W. Q.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 7134.
[13] Furuya, T.; Kuttruff, C. A.; Ritter, T. Curr. Opin. Drug Discov. Devel. 2008, 11, 803.
[14] Tang, P.; Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2010, 132, 12150.
[15] Sun, H.; Dimagno, S. G. Angew. Chem., Int. Ed. 2006, 45, 2720.
[16] Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 2219.
[17] Barker, T. J.; Boger, D. L. J. Am. Chem. Soc. 2012, 134, 13588.
[18] Liu, W.; Huang, X. Y.; Cheng, M. J.; Nielsen, R. J.; William, A. G. I.; Groves, J. T. Science 2012, 337, 1322.
[19] Yin, F.; Wang, Z.; Li, Z., Li, C. J. Am. Chem. Soc. 2012, 134, 10401.
[20] Chen, H.; Wang, X.; Guo, M.; Zhao, W.; Tang, X.; Wang, G. Org. Chem. Front. 2017, 4, 2403.
[21] Zhou, N.; Xu, P.; Li, W.; Cheng, Y.; Zhu, C. Acta Chim. Sinica 2017, 75, 60(in Chinese). (周能能, 胥攀, 李伟鹏, 成义祥, 朱成建, 化学学报, 2017, 75, 60.)
[22] Amii, H.; Uneyana, K. Chem. Rev. 2009, 109, 2119.
[23] Aizenberg, M.; Milstein, D. Science 1994, 265, 359.
[24] Peterson, A. A.; McNeill, K. Organometallics 2006, 25, 4938.
[25] Ishii, Y.; Chatani, N.; Yorimitsu, S.; Murai, S. Chem. Lett. 1998, 27, 157.
[26] Bohm, V. P. W.; Gstottmayr, C. W. K.; Weskamp, T.; Herrmann, W. A. Angew. Chem., Int. Ed. 2001, 40, 3387.
[27] Braun, T.; Perutz, R. N.; Sladek, M. I. Chem. Commun. 2001, 21, 2254.
[28] Mongin, F.; Mojovic, L.; Guillamet, B.; Trecourt, C. F.; Queguiner, G. J. Org. Chem. 2002, 67, 8991.
[29] Schaub, T.; Backes, M.; Radius, U. J. Am. Chem. Soc. 2006, 128, 15964.
[30] Widdowson, D. A.; Wilhelm, R. Chem. Commun. 2000, 1, 2211.
[31] Kim, Y.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696.
[32] Cargill, M. R.; Sanford, G.; Tadeusiak, A. J.; Yufit, D. S.; Howard, J. A.; Kilickiran, P.; Nelles, G. J. Org. Chem. 2010, 75, 5860.
[33] Mikami, K.; Miyamoto, T.; Hatano, M. Chem. Commun. 2004, 2082.
[34] Douvris, C.; Ozerov, O. V. Science 2008, 321, 1188.
[35] Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 12644.
[36] Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 19880.
[37] Watson, D. A.; Su, M.; Teverovskiy, G.; Zhang, Y.; García-Fortanet, J.; Kinzel, T.; Buchwald, S. L. Science 2009, 325, 1661.
[38] Chu, L. L.; Qing, F. L. J. Am. Chem. Soc. 2010, 132, 7262.
[39] Chu, L. L.; Qing, F. L. Org. Lett. 2010, 12, 5060.
[40] Liu, T. F.; Shen, Q. L. Org. Lett. 2011, 13, 2342.
[41] Liu, T. F.; Shao, X. X.; Wu, Y. M.; Shen, Q. L. Angew. Chem., Int. Ed. 2012, 51, 540.
[42] Prakash, G. K. S.; Hu, J. B. Acc. Chem. Res. 2007, 40, 921.
[43] Zhao, Y. C.; Huang, W. Z.; Zhu, L. G.; Hu, J. B. Org. Lett. 2010, 12, 1444.
[44] Zhou, Q. H.; Ruffoni, A.; Gianatassio, R.; Fujiwara, Y.; Sella, E.; Shabat, D.; Baran, P. S. Angew. Chem., Int. Ed. 2013, 52, 3949.
[45] Rong, J.; Ni, C.; Wang, Y.; Kuang, C.; Gu, Y.; Hu, J. Acta Chim. Sinica 2017, 75, 105(in Chinese). (荣健, 倪传法, 王云泽, 匡翠文, 顾玉诚, 胡金波, 化学学报, 2017, 75, 105.)
[46] Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754.
[47] Do, H. Q.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 1128.
[48] He, C. Y.; Fan, S. L.; Zhang, X. G. J. Am. Chem. Soc. 2010, 132, 12850.
[49] Zhang, X. G.; Fan, S. L.; He, C. Y.; Wan, X.; Min, Q. Q.; Yang, J.; Jiang, Z. X. J. Am. Chem. Soc. 2010, 132, 4506.
[50] Zeng, Y. W.; Zhang, L. J.; Zhao, Y. C.; Ni, C. F.; Zhao, J. W.; Hu, J. B. J. Am. Chem. Soc. 2013, 135, 2955.
[51] Wang, X.; Xu, Y.; Mo, F.; Ji, G. J.; Qiu, D.; Feng, J. J.; Ye, Y. X.; Zhang, S. N.; Zhang, Y.; Wang, J. B. J. Am. Chem. Soc. 2013, 135, 10330.
[52] Dai, J. J.; Fang, C.; Xiao, B.; Yi, J.; Xu, J.; Liu, Z. J.; Lu, X.; Liu, L.; Fu, Y. J. Am. Chem. Soc. 2013, 135, 8436.
[53] Lewis, G. N.; Macdonald, R. T. J. Am. Chem. Soc. 1936, 58, 2519.
[54] Jeon, Y. S.; Jang, N. H.; Kang, B. M.; Jeon, Y. S.; Kim, C. S.; Chio, K. Y.; Ryu, H. Bull. Korean Chem. Soc. 2007, 28, 451.
[55] Kim, D. W. J. Radioanal. Nucl. Chem. 2002, 252, 559.
[56] Takahashi, H.; Zhang, Y. H.; Miyajima, T.; Oi, T. J. Mater. Chem. 2006, 16, 1462.
[57] Kim, D. W.; Kang, B. M.; Jeon, B. K.; Joen, Y. S. J. Radioanal. Nucl. Chem. 2003, 256, 81.
[58] Araki, H.; Umeda, M.; Enokida, Y.; Yamamoto, I. Fusion. Eng. Des. 1998, 39, 1009.
[59] Otake, K.; Suzuki, T.; Kim, H. J.; Nomura, M.; Fujii, Y. J. Nucl. Sci. Technol. 2006, 43, 419.
[60] Black, J. R.; Umeda, G.; Dunn, B.; Mcdonough, W. F.; Kavner, A. J. Am. Chem. Soc. 2009, 131, 9904.
[61] Saleem, M.; Hussain, S.; Rafiq, M.; Baig, M. A. J. Appl. Phys. 2006, 100, 053111-1.
[62] Olivares, I. E.; Duarte, A. E.; Saravia, E. A.; Duarte, F. J. Appl. Opt. 2002, 41, 2973.
[63] Shanghai Institute of Organic Chemistry, CAS. ZL2012104371552, 2012. (中国科学院上海有机化学研究所, ZL2012104371552, 2012.)
[64] Hu, J. B.; Zhang, W.; Zheng, W. Q.; Chen, G. H.; Shi, X.; Xu, Y. C.; Lv, H. G.; Yuan, C. Y. ZL201310239535X, 2013. (胡金波, 张伟, 郑卫琴, 陈光华, 施啸, 徐永昌, 吕红贵, 袁承业, ZL201310239535X, 2013.)
[65] Hu, J. B.; Zhang, W.; Zheng, W. Q.; Shi, X.; Xu, Y. C.; Lv, H. G.; Yuan, C. Y. ZL2013102395326, 2013. (胡金波, 张伟, 郑卫琴, 施啸, 徐永昌, 吕红贵, 袁承业, ZL2013102395326, 2013.)
[66] Shanghai Institute of Organic Chemistry, CAS. PCT/CN2013/075340, 2013.
[67] Hu, J. B.; Zhang, W.; Zheng, W. Q.; Chen, G. H.; Shi, X.; Xu, Y. C.; Lv, H. G.; Yuan, C. Y. PCT/CN2014/074304, 2014.
[68] Hu, J. B.; Zhang, W.; Xu, Y. C.; Gu, H. X. CN2017103408158, 2017. (胡金波, 张伟, 徐永昌, 顾洪熙, CN2017103408158, 2017.)
[69] Hu, J. B.; Zhang, W.; Zhang, L. J. CN2017103398796, 2017. (胡金波, 张伟, 张丽君. CN2017103398796, 2017.)
[70] Hu, J. B.; Zhang, W.; Gu, H. X. Zheng, W. Q. CN2017103398917, 2017. (胡金波, 张伟, 顾洪熙, 郑卫琴, CN2017103398917, 2017.)
[71] Hu, J. B.; Zhang, W.; Zheng, W. Q. Xu, Y. C. CN2017103398936, 2017. (胡金波, 张伟, 郑卫琴, 徐永昌, CN2017103398936, 2017.)
[72] Mahl, A.; Lim, A.; Latta, J.; Yemam, H. A.; Greife, U.; Sellinger, A. Nucl. Instrum. Methods Phys. Res. A 2018, 884, 113.
[73] Babb, D. A.; Ezzell, B. R.; Clement, K. S.; Richey, W. F.; Kennedy, A. P. J. Polym. Sci. Polym. Chem. 1993, 31, 3465.
[74] Zhu, Y. Q.; Huang, Y. G.; Meng, W. D.; Li, H.; Qing, F. L. Polymer 2006, 47, 6272.
[75] Yao, R. X.; Kong, L.; Yin, Z. S.; Qing, F. L. J. Fluorine Chem. 2008, 129, 1003.
[76] Li, Y. J.; Chen, S.; Zhang, S.; Li, Q. N.; Lu, G. L.; Li, W. X.; Liu, H.; Huang, X. Y. Polymer 2009, 50, 5192.
[77] Wang, Q.; Yu, X.; Jin, J.; Wu, Y.; Liang, Y. Chin. J. Chem. 2018, 36, 223.
[78] Watanabe, Y.; Shibasaki, Y.; Ando, S.; Ueda, M. Polym J. 2006, 38, 79.
[79] Towery, D.; Fury, M. A. J. Electron. Mater. 1998, 27, 1088.
[80] Tsuchiya, K.; Shibasaki, Y.; Aoyagi, M.; Ueda, M. Macromolecules 2006, 39, 3964.
[81] Niu, Y. M.; Zhu, X. L.; Liu, L. Z.; Zhang, Y.; Wang, G. B.; Jiang, Z. H. React. Funct. Polym. 2006, 66, 559.
[82] Dang, T. D.; Mather, P. T.; Alexander, M. D.; Grayson, C. J.; Houtz, M. D.; Spry, R. J.; Arnold, F. E. J. Polym. Sci. Polym. Chem. 2000, 38, 1991.
[83] Fukukawa, K.; Shibasakl, Y.; Ueda, M. Macromolecules 2004, 37, 8256.
[84] Su, Y. C.; Chang, F. C. Polymer 2003, 44, 7989.
[85] Sharangpani, R.; Singh, R. Rev. Sci. Instrum. 1997, 68, 1564.
[86] Rosenmeyer, C. T.; Wu, H. MRS Proceedings 1996, 427, 463.
[87] Luo, Y. J.; Jin, K. K.; He, C. Q.; Wang, J. J.; Sun, J.; He, F. K.; Zhou, J. F.; Wang, Y. Q.; Fang, Q. Macromolecules 2016, 49, 7314.
[88] Wang, J. J.; Sun, J.; Zhou, J. F.; Jin, K. K.; Fang, Q. ACS Appl. Mater. Interfaces 2017, 9, 12782.
[89] Wang, J. J.; Zhou, J. F.; Jin, K. K.; Wang, L.; Sun, J.; Fang, Q. Macromolecules 2017, 50, 9394.
[90] Zhao, Z.; Ni, H.; Han, Z.; Jiang, T.; Xu, Y.; Lu, X.; Ye, P. ACS Appl. Mater. Interfaces 2013, 5, 7808.
[91] Cheng, Y. Acta Polym. Sinica 2017, 8, 1234.
[92] Jha, S. K.; Mishra, V. K.; Sharma, D. K.; Damodaran, T. Rev. Environ. Contam. Toxicol. 2011, 211, 121.
[93] Lau, C.; Butenhoff, J. L.; Rogers, J. M. Toxicol. Appl. Pharm. 2004, 198, 231.
[94] Dewitt, J. C.; Shnyra, A.; Badr, M. Z.; Loveless, S. E.; Hoban, D.; Frame, S. R.; Cunard, R.; Anderson, S. E.; Meade, B. J.; Peden-Adams, M. M.; Luebke, R. W.; Luster, M. I. Crit. Rev. Toxicol. 2009, 39, 76.
[95] Younglai, E. V.; Wu, Y. J.; Foster, W. G. Curr. Pharm. Design 2007, 13, 3005.
[96] Yao, W. Q.; Li, Y. J.; Huang, X. Y. Polymer 2014, 55, 6197.
[97] Tong, L.; Shen, Z.; Zhang, S.; Li, Y. J.; Lu, G. L.; Huang, X. Y. Polymer 2008, 49, 4534.
[98] Wang, X.; Cheng, W. G.; Yang, Q. Y.; Niu, H. Y.; Liu, Q.; Liu, Y.; Gao, M.; Xu, M.; Xu, A.; Liu, S. J.; Huang, X. Y.; Du, Y. G. J. Environ. Sci. 2018, 69, 217.

耐极端条件含氟材料的研究进展

Recent Advances in Fluorine-containing Materials with Extreme Environment Resistance

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Rong Zhuang, Xiaosa Xu, Changzhen Qu, Shunqi Xu, Tao Yu, Hongqiang Wang, Fei Xu. Recent Progress of Porous Polymers for Lithium Metal Anodes Protection [J]. Acta Chimica Sinica, 2021, 79(4): 378-387.
[2]	Miao Yu, Wu Zhao, Kai Zhang, Xin Guo. Single-Molecule Mechanism of pH Sensitive Smart Polymer [J]. Acta Chimica Sinica, 2021, 79(4): 500-505.
[3]	Lele Li, Yangyang Xiang, Huan Liu, Shuanhong Ma, Bin Li, Zhengfeng Ma, Qiangbing Wei, Bo Yu, Feng Zhou. Temperature-Responsive Nanofibrous Membranes Fabricated by Subsurface-Initiated Atom Transfer Radical Polymerization for Controllable Oil/Water Separation [J]. Acta Chimica Sinica, 2021, 79(3): 353-360.
[4]	Su Zhan, Fuxiang Zhang. Recent Progress on Electrocatalytic Synthesis of Ammonia Under Amibent Conditions [J]. Acta Chimica Sinica, 2021, 79(2): 146-157.
[5]	Weihua Li. “Bridge” Makes Differences to the Self-assembly of Block Copolymers [J]. Acta Chimica Sinica, 2021, 79(2): 133-138.
[6]	Hui He, Lingli Zhou, Zhen Liu. Advances in Protein Biomarker Assay via the Combination of Molecular Imprinting and Surface-enhanced Raman Scattering [J]. Acta Chimica Sinica, 2021, 79(1): 45-57.
[7]	Feng Boxu, Zhuang Xiaodong. Carbon-Enriched meso-Entropy Materials: from Theory to Cases [J]. Acta Chimica Sinica, 2020, 78(9): 833-847.
[8]	Feng Sheng, Gao Wenbo, Cao Hujun, Guo Jianping, Chen Ping. Advances in the Chemical Looping Ammonia Synthesis [J]. Acta Chimica Sinica, 2020, 78(9): 916-927.
[9]	Sun Qi, Xiao Feng-Shou. Exploration of Porous Organic Polymers as a Platform for Biomimetic Catalysis [J]. Acta Chimica Sinica, 2020, 78(9): 827-832.
[10]	Zhang Lan, Ma Suqian, Wang Hanbing, Liang Yunhong, Zhang Zhihui. Research Progress of Shape Memory Polymer Deformation Mode [J]. Acta Chimica Sinica, 2020, 78(9): 865-876.
[11]	Xu Weichang, Liu Wei, Li Xiang, Xu Peng, Yu Biao. Synthesis of Oligosaccharides Relevant to the Substrates of Heparanase via Dehydrative Glycosylation [J]. Acta Chimica Sinica, 2020, 78(8): 767-777.
[12]	Wei Zheyu, Chang Yalin, Yu Han, Han Sheng, Wei Yongge. Application of Anderson Type Heteropoly Acids as Catalysts in Organic Synthesis [J]. Acta Chimica Sinica, 2020, 78(8): 725-732.
[13]	Chen Yougen, Ding Yuansheng. Recent Progress of Organocatalyzed Group Transfer Polymerization [J]. Acta Chimica Sinica, 2020, 78(8): 733-745.
[14]	Jiang Jinhui, Zhu Yunqing, Du Jianzhong. Challenges and Perspective on Ring-Opening Polymerization-Induced Self-Assembly [J]. Acta Chimica Sinica, 2020, 78(8): 719-724.
[15]	Wu Qianye, Zhang Chenxi, Sun Kang, Jiang Hai-Long. Microwave-Assisted Synthesis and Photocatalytic Performance of a Soluble Porphyrinic MOF [J]. Acta Chimica Sinica, 2020, 78(7): 688-694.