Citation: Song Bo, Qin Anjun, Tang Ben Zhong. New Polymerizations Based on Green Monomer of Carbon Dioxide[J]. Acta Chimica Sinica, ;2020, 78(1): 9-22. doi: 10.6023/A19090340 shu

New Polymerizations Based on Green Monomer of Carbon Dioxide

Song Bo ^a ,
Qin Anjun ^a,, ,
Tang Ben Zhong ^a,b,,

a.
State Key Laboratory of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates, Center for Aggregation-Induced Emission, South China University of Technology, Guangzhou 510640
b.
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, The Hong Kong University of Science & Technology, Hong Kong

Corresponding author: Qin Anjun, msqinaj@scut.edu.cn Tang Ben Zhong, tangbenz@ust.hk
Received Date: 15 September 2019
Available Online: 31 January 2019
Fund Project: the National Natural Science Foundation of China 21490571the Natural Science Foundation of Guangdong Province 2016A030312002the National Natural Science Foundation of China 21788102the National Natural Science Foundation of China 21525417the Innovation and Technology Commission of Hong Kong ITC-CNERC14S01Project supported by the National Natural Science Foundation of China (Nos. 21788102, 21525417, 21490571), the Natural Science Foundation of Guangdong Province (Nos. 2016A030312002, 2019B030301003), and the Innovation and Technology Commission of Hong Kong (ITC-CNERC14S01)the Natural Science Foundation of Guangdong Province 2019B030301003

Figures(41)

Carbon dioxide (CO₂) is an abundant, inexpensive, non-toxic and renewable C1 resource, and it is also a kind of green monomer. The polymerizations based on CO₂ have been one of the hot research topics. The copolymerization of CO₂ and epoxide monomers was widely studied in the past few years and has been industrialized. Some new polymerizations based on CO₂ have also been reported recently. There are two ways to produce polymeric materials from CO₂. One is converting CO₂ into monomers for further ring opening or step growth polymerizations, such as lactone, cyclic carbonates, furan-2, 5-dicarboxylic acid. Another is directly using CO₂ as a monomer for the copolymerization with other monomers to generate polymers. They are both significant for developing new polymerizations based on CO₂ and expanding CO₂-based polymeric materials. The advances in converting CO₂ into polymeric materials during the past few years are summarized in this review and the perspective in this area is discussed.
- carbon dioxide,
- alkyne monomer,
- cyclic carbonate,
- lactone,
- furan-2, 5-dicarboxylic acid
1. [1]
  Liu, Q.; Wu, L.; Jackstell, R.; Beller, M. Nat. Commun. 2015, 6, 5933. doi: 10.1038/ncomms6933
2. [2]
  Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365. doi: 10.1021/cr068357u
3. [3]
  Du, P.; Su, T.; Luo, X.; Zhou, X.; Qin, Z.; Ji, H.; Chen, J. Chin. J. Chem. 2018, 36, 538. doi: 10.1002/cjoc.201700761
4. [4]
  Zhang, F. H.; Liu, C.; Li, W.; Tian, G. L.; Xie, J. H.; Zhou, Q. L. Chin. J. Chem. 2018, 36, 1000. doi: 10.1002/cjoc.201800278
5. [5]
  Zhang, W.; Zhang, N.; Guo, C.; Lü, X. B. Chin. J. Org. Chem. 2017, 37, 1309. doi: 10.6023/cjoc201701031
6. [6]
  Cao, Y.; He, X.; Wang, N.; Li, H. R.; He, L. N. Chin. J. Chem. 2018, 36, 644. doi: 10.1002/cjoc.201700742
7. [7]
  Qi, C.; Yan, D.; Xiong, W.; Jiang, H. Chin. J. Chem. 2018, 36, 399. doi: 10.1002/cjoc.201700808
8. [8]
  Xu, P.; Wang, S. Y.; Fang, Y.; Ji, S. J. Chin. J. Org. Chem. 2018, 38, 1626.
9. [9]
  Inoue, S.; Koinuma, H.; Tsuruta, T. J. Polym. Sci., Part C: Polym. Lett. 1969, 7, 287. doi: 10.1002/pol.1969.110070408
10. [10]
  Lu, X. B.; Darensbourg, D. J. Chem. Soc. Rev. 2012, 41, 1462. doi: 10.1039/C1CS15142H
11. [11]
  Lu, X. B.; Ren, W. M.; Wu, G. P. Acc. Chem. Res. 2012, 45, 1721. doi: 10.1021/ar300035z
12. [12]
  Li, Y.; Zhang, Y. Y.; Liu, B.; Zhang, X. H. Chin. J. Polym. Sci. 2018, 36, 139. doi: 10.1007/s10118-018-2047-5
13. [13]
  Li, Y.; Zhang, Y. Y.; Hu, L. F.; Zhang, X. H.; Du, B. Y.; Xu, J. T. Prog. Polym. Sci. 2018, 82, 120. doi: 10.1016/j.progpolymsci.2018.02.001
14. [14]
  Darensbourg, D. J.; Mackiewicz, R. M.; Phelps, A. L.; Billodeaux, D. R. Acc. Chem. Res. 2004, 37, 836. doi: 10.1021/ar030240u
15. [15]
  Darensbourg, D. J. Chem. Rev. 2007, 107, 2388. doi: 10.1021/cr068363q
16. [16]
  Trott, G.; Saini, P. K.; Williams, C. K. Philos. Trans. R. Soc., A 2016, 374, 20150085. doi: 10.1098/rsta.2015.0085
17. [17]
  Cheng, M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1998, 120, 11018. doi: 10.1021/ja982601k
18. [18]
  Coates, G. W.; Moore, D. R. Angew. Chem., Int. Ed. 2004, 43, 6618. doi: 10.1002/anie.200460442
19. [19]
  Sugimoto, H.; Inoue, S. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 5561. doi: 10.1002/pola.20319
20. [20]
  Noh, E. K.; Na, S. J.; Sujith, S.; Kim, S. W.; Lee, B. Y. J. Am. Chem. Soc. 2007, 129, 8082. doi: 10.1021/ja071290n
21. [21]
  Ohkawara, T.; Suzuki, K.; Nakano, K.; Mori, S.; Nozaki, K. J. Am. Chem. Soc. 2014, 136, 10728. doi: 10.1021/ja5046814
22. [22]
  Wang, Y.; Qin, Y.; Wang, X.; Wang, F. ACS Catal. 2015, 5, 393. doi: 10.1021/cs501719v
23. [23]
  Zhuo, C.; Qin, Y.; Wang, X.; Wang, F. Chin. J. Chem. 2018, 36, 299. doi: 10.1002/cjoc.201800019
24. [24]
  Luo, M.; Li, Y.; Zhang, Y. Y.; Zhang, X. H. Polymer 2016, 82, 406. doi: 10.1016/j.polymer.2015.11.011
25. [25]
  Sasaki, Y.; Inoue, Y.; Hashimoto, H. J. Chem. Soc., Chem. Commun. 1976, 15, 605.
26. [26]
  Musco, A.; Perego, C.; Tartiari, V. Inorg. Chim. Acta 1978, 28, 147. doi: 10.1016/S0020-1693(00)87385-5
27. [27]
  Behr, A.; Juszak, K.-D. J. Org. Chem. 1983, 255, 263. doi: 10.1016/0022-328X(83)87028-4
28. [28]
  Braunstein, P.; Matt, D.; Nobel, D. J. Am. Chem. Soc. 1988, 110, 3207. doi: 10.1021/ja00218a033
29. [29]
  Dinjus, E.; Leitner, W. Appl. Org. Chem. 1995, 9, 43. doi: 10.1002/aoc.590090108
30. [30]
  Pitter, S.; Dinjus, E. J. Mol. Catal. Chem. 1997, 125, 39. doi: 10.1016/S1381-1169(97)00081-2
31. [31]
  Beller, M.; Bolm, C. ChemInform 1998, 36, 211.
32. [32]
  Nakano, R.; Ito, S.; Nozaki, K. Nat. Chem. 2014, 6, 325. doi: 10.1038/nchem.1882
33. [33]
  Liu, M.; Sun, Y.; Liang, Y.; Lin, B. L. ACS Macro Lett. 2017, 1373.
34. [34]
  Zhang, Y.; Xia, J.; Song, J.; Zhang, J.; Ni, X.; Jian, Z. Macromolecules 2019, 52, 2504. doi: 10.1021/acs.macromol.9b00195
35. [35]
  Xu, Y.-C.; Zhou, H.; Sun, X.-Y.; Ren, W.-M.; Lu, X. B. Macromolecules 2016, 49, 5782. doi: 10.1021/acs.macromol.6b01372
36. [36]
  Calo, V.; Nacci, A.; Monopoli, A.; Fanizzi, A. Org. Lett. 2002, 4, 2561. doi: 10.1021/ol026189w
37. [37]
  Kihara, N.; Hara, N.; Endo, T. J. Org. Chem. 1993, 58, 6198. doi: 10.1021/jo00075a011
38. [38]
  Song, J. L.; Zhang, Z. F.; Han, B. X.; Hu, S. Q.; Li, W. J.; Xie, Y. Green Chem. 2008, 10, 1337. doi: 10.1039/b815105a
39. [39]
  Xie, Y.; Zhang, Z. F.; Jiang, T.; He, J. L.; Han, B. X.; Wu, T. B.; Ding, K. L. Angew. Chem. In. Ed. 2007, 46, 7255. doi: 10.1002/anie.200701467
40. [40]
  Gu, Y.; Shi, F.; Deng, Y. J. Org. Chem. 2004, 69, 391. doi: 10.1021/jo0351365
41. [41]
  Song, Q. W.; Yu, B.; Li, X. D.; Ma, R.; Diao, Z. F.; Li, R. G.; Li, W.; He, L. N. Green Chem. 2014, 16, 1633. doi: 10.1039/c3gc42406e
42. [42]
  Song, Q.-W.; He, L.-N. Adv. Synth. Catal. 2016, 358, 1251. doi: 10.1002/adsc.201500639
43. [43]
  Eghbali, N.; Li, C. J. Green Chem. 2007, 9, 213. doi: 10.1039/B615612F
44. [44]
  Wang, J. L.; Wang, J. Q.; He, L. N.; Dou, X. Y.; Wu, F. Green Chem. 2008, 10, 1218. doi: 10.1039/b807108j
45. [45]
  Gennen, S.; Grignard, B.; Tassaing, T.; Jerome, C.; Detrembleur, C. Angew. Chem., Int. Ed. 2017, 56, 10394. doi: 10.1002/anie.201704467
46. [46]
  Gennen, S.; Grignard, B.; Jérôme, C.; Detrembleur, C. Adv. Synth. Catal. 2019, 361, 355. doi: 10.1002/adsc.201801230
47. [47]
  Liu, B.; Zhang, X. H. Gen. Chem. 2018, 4, 180007. doi: 10.21127/yaoyigc20180007
48. [48]
  Ouhib, F.; Grignard, B.; Van Den Broeck, E.; Luxen, A.; Robeyns, K.; Van Speybroeck, V.; Jerome, C.; Detrembleur, C. Angew. Chem., Int. Ed. 2019, 58, 11768. doi: 10.1002/anie.201905969
49. [49]
  Banerjee, A.; Dick, G. R.; Yoshino, T.; Kanan, M. W. Nature 2016, 531, 215. doi: 10.1038/nature17185
50. [50]
  Kadokawa, J.; Habu, H.; Fukamachi, S.; Karasu, M.; Tagaya, H.; Chiba, K. Macromol. Rapid Commun. 1998, 19, 657. doi: 10.1002/(SICI)1521-3927(19981201)19:12<657::AID-MARC657>3.0.CO;2-R
51. [51]
  Tamura, M.; Ito, K.; Honda, M.; Nakagawa, Y.; Sugimoto, H.; Tomishige, K. Sci. Rep. 2016, 6, 24038. doi: 10.1038/srep24038
52. [52]
  Oi, S.; Nemoto, K.; Matsuno, S.; Inoue, Y. Macromol. Rapid Commun. 1994, 15, 133. doi: 10.1002/marc.1994.030150207
53. [53]
  Chen, Z. L.; Hadjichristidis, N.; Feng, X. S.; Gnanou, Y. Polym. Chem. 2016, 7, 4944. doi: 10.1039/C6PY00783J
54. [54]
  Yamazaki, N.; Higashi, F.; Iguchi, T. J. Polym. Sci. Polym. Lett. Ed. 1974, 12, 517. doi: 10.1002/pol.1974.130120904
55. [55]
  Yamazaki, N.; Nakahama, S.; Higashi, F. Ind. Eng. Chem. Prod. Res. Dev. 1979, 18, 249.
56. [56]
  Wu, C. Y.; Wang, J. Y.; Chang, P. J.; Cheng, H. Y.; Yu, Y. C.; Wu, Z. J.; Dong, D. W.; Zhao, F. Y. Phys. Chem. Chem. Phys. 2012, 14, 464. doi: 10.1039/C1CP23332G
57. [57]
  Wu, P.-X.; Cheng, H.-Y.; Shi, R.-H.; Jiang, S.; Wu, Q.-F.; Zhang, C.; Arai, M.; Zhao, F.-Y. Adv. Synth. Catal. 2019, 361, 317. doi: 10.1002/adsc.201801134
58. [58]
  Chen, Z.; Hadjichristidis, N.; Feng, X.; Gnanou, Y. Macromolecules 2017, 50, 2320. doi: 10.1021/acs.macromol.7b00142
59. [59]
  Yoo, W. J.; Li, C. J. Adv. Synth. Catal. 2008, 350, 1503. doi: 10.1002/adsc.200800232
60. [60]
  Zhao, J. W.; Huang, H. W.; Qi, C. R.; Jiang, H. F. Eur. J. Org. Chem. 2012, 29, 5665.
61. [61]
  Yu, B.; Cheng, B. B.; Liu, W. Q.; Li, W.; Wang, S. S.; Cao, J.; Hu, C. W. Adv. Synth. Catal. 2016, 358, 90. doi: 10.1002/adsc.201500921
62. [62]
  Teffahi, D.; Hocine, S.; Li, C. J. Lett. Org. Chem. 2012, 9, 585. doi: 10.2174/157017812802850221
63. [63]
  Ugi, I.; Meyr, R.; Fetzer, U. Angew. Chem. 1959, 71, 386.
64. [64]
  Ugi, I.; Steinbruckner, C. Chem. Ber. 1961, 94, 2802. doi: 10.1002/cber.19610941032
65. [65]
  Sehlinger, A.; Schneider, R.; Meier, M. A. Macromol. Rapid Commun. 2014, 35, 1866.
66. [66]
  Tsuda, T.; Maruta, K.; Kitaike, Y. J. Am. Chem. Soc. 1992, 114, 1498. doi: 10.1021/ja00030a065
67. [67]
  Oi, S.; Fukue, Y.; Nemoto, K.; Inoue, Y. Macromolecules 1996, 29, 2694. doi: 10.1021/ma9514784
68. [68]
  Song, B.; He, B.; Qin, A.; Tang, B. Z. Macromolecules 2018, 51, 42. doi: 10.1021/acs.macromol.7b02109
69. [69]
  Fu, W.; Dong, L.; Shi, J.; Tong, B.; Cai, Z.; Zhi, J.; Dong, Y. Polym. Chem. 2018, 9, 5543. doi: 10.1039/C8PY01336E
70. [70]
  Song, B.; Bai, T.; Xu, X.; Chen, X.; Liu, D.; Guo, J.; Qin, A.; Ling, J.; Tang, B. Z. Macromolecules 2019, 52, 5546. doi: 10.1021/acs.macromol.9b00898
71. [71]
  Mömming, C. M.; Otten, E.; Kehr, G.; Fröhlich, R.; Grimme, S.; Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2009, 48, 6643. doi: 10.1002/anie.200901636
72. [72]
  Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46. doi: 10.1002/anie.200903708
73. [73]
  Stephan, D. W. Science 2016, 354, aaf7229. doi: 10.1126/science.aaf7229
74. [74]
  Liu, R.; Liu, X.; Ouyang, K.; Yan, Q. ACS Macro Lett. 2019, 8, 200. doi: 10.1021/acsmacrolett.9b00066
1. [1]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
2. [2]
  Xiaoning TANG , Shu XIA , Jie LEI , Xingfu YANG , Qiuyang LUO , Junnan LIU , An XUE . Fluorine-doped MnO₂ with oxygen vacancy for stabilizing Zn-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1671-1678. doi: 10.11862/CJIC.20240149
3. [3]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
4. [4]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
5. [5]
  Chunmei GUO , Weihan YIN , Jingyi SHI , Jianhang ZHAO , Ying CHEN , Quli FAN . Facile construction and peroxidase-like activity of single-atom platinum nanozyme. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1633-1639. doi: 10.11862/CJIC.20240162
6. [6]
  Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn²⁺ doped quasi-two-dimensional perovskites (PEA)₂Pb_yMn_1-yBr₄. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
7. [7]
  Muhammad Humayun , Mohamed Bououdina , Abbas Khan , Sajjad Ali , Chundong Wang . Designing single atom catalysts for exceptional electrochemical CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(1): 100193-100193. doi: 10.1016/j.cjsc.2023.100193
8. [8]
  Hong Dong , Feng-Ming Zhang . Covalent organic frameworks for artificial photosynthetic diluted CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(7): 100307-100307. doi: 10.1016/j.cjsc.2024.100307
9. [9]
  Ping Wang , Tianbao Zhang , Zhenxing Li . Reconstruction mechanism of Cu surface in CO2 reduction process. Chinese Journal of Structural Chemistry, 2024, 43(8): 100328-100328. doi: 10.1016/j.cjsc.2024.100328
10. [10]
  Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO₂ adsorption and conversion: Modification methods, reaction condition, and CO₂ hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
11. [11]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
12. [12]
  Maomao Liu , Guizeng Liang , Ningce Zhang , Tao Li , Lipeng Diao , Ping Lu , Xiaoliang Zhao , Daohao Li , Dongjiang Yang . Electron-rich Ni2+ in Ni3S2 boosting electrocatalytic CO2 reduction to formate and syngas. Chinese Journal of Structural Chemistry, 2024, 43(8): 100359-100359. doi: 10.1016/j.cjsc.2024.100359
13. [13]
  Shu-Ran Xu , Fang-Xing Xiao . Metal halide perovskites quantum dots: Synthesis, and modification strategies for solar CO2 conversion. Chinese Journal of Structural Chemistry, 2023, 42(12): 100173-100173. doi: 10.1016/j.cjsc.2023.100173
14. [14]
  Tianbo Jia , Lili Wang , Zhouhao Zhu , Baikang Zhu , Yingtang Zhou , Guoxing Zhu , Mingshan Zhu , Hengcong Tao . Modulating the degree of O vacancy defects to achieve selective control of electrochemical CO₂ reduction products. Chinese Chemical Letters, 2024, 35(5): 108692-. doi: 10.1016/j.cclet.2023.108692
15. [15]
  Yufei Jia , Fei Li , Ke Fan . Surface reconstruction of Cu-based bimetallic catalysts for electrochemical CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(3): 100255-100255. doi: 10.1016/j.cjsc.2024.100255
16. [16]
  Ziruo Zhou , Wenyu Guo , Tingyu Yang , Dandan Zheng , Yuanxing Fang , Xiahui Lin , Yidong Hou , Guigang Zhang , Sibo Wang . Defect and nanostructure engineering of polymeric carbon nitride for visible-light-driven CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(3): 100245-100245. doi: 10.1016/j.cjsc.2024.100245
17. [17]
  Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO₂ reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112
18. [18]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
19. [19]
  Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO₂. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364
20. [20]
  Xueyang Zhao , Bangwei Deng , Hongtao Xie , Yizhao Li , Qingqing Ye , Fan Dong . Recent process in developing advanced heterogeneous diatomic-site metal catalysts for electrochemical CO₂ reduction. Chinese Chemical Letters, 2024, 35(7): 109139-. doi: 10.1016/j.cclet.2023.109139

Get Citation

PDF

XML

Metrics

PDF Downloads(68)
Abstract views(2171)
HTML views(630)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142