Citation: Xiaoqing Wang, Yuqing Bai, Xiaoyong Zhai, Bo Wu, Yonggui Zhou. Synthesis of poly(silyl ether)s via copper-catalyzed dehydrocoupling polymerization[J]. Chinese Chemical Letters, ;2022, 33(5): 2639-2642. doi: 10.1016/j.cclet.2021.09.054 shu

Synthesis of poly(silyl ether)s via copper-catalyzed dehydrocoupling polymerization

Xiaoqing Wang ^{a, b} ,
Yuqing Bai ^a ,
Xiaoyong Zhai ^a ,
Bo Wu ^{a, *,} ,
Yonggui Zhou ^{a, *,}

a.
Department of Fine Chemicals, State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China

bowu@dicp.ac.cn

ygzhou@dicp.ac.cn

Received Date: 16 July 2021
Revised Date: 8 September 2021
Accepted Date: 14 September 2021
Available Online: 22 September 2021

Figures(1)

The development of efficient method to prepare poly(silyl ether)s (PSEs) is highly desirable. Herein, an environmentally sustainable copper-catalyzed dehydrocoupling polymerization was developed with good yields and high molecular weight (up to 48, 400 of Mn and up to 97% yield). Monomers of different types (AB type or AA and BB type) are suitable to afford PSEs. The PSEs show good thermal stability and low glass-transition temperature.
- Poly(silyl ether)s,
- CuH catalysis,
- Dehydrocoupling,
- Environmental and economic benign,
- Good thermal stability
1. [1]
  K.J. Shea, D.A. Loy, O. Webster, J. Am. Chem. Soc. 114 (1992) 6700-6710. doi: 10.1021/ja00043a014
2. [2]
  U. Lauter, S.W. Kantor, K. Schmidt-Rohr, W.J. MacKnight, Macromolecules 32 (1999) 3426-3431. doi: 10.1021/ma981292f
3. [3]
  Y. Liu, I. Imae, A. Makishima, Y. Kawakami, Sci. Technol. Adv. Mater. 4 (2003) 27-34. doi: 10.1016/S1468-6996(03)00021-4
4. [4]
  Y. Wang, R. Yang, Z. Shi, et al., ACS Nano 5 (2011) 3645-3650. doi: 10.1021/nn103523t
5. [5]
  S. Ahmed, H.K. Yang, A.E. Ozcam, et al., Biomacromolecules 12 (2011) 1265-1271. doi: 10.1021/bm101549y
6. [6]
  M. Henot, E. Drockenmuller, L. Leger, F. Restagno, ACS Macro Lett. 7 (2018) 112-115. doi: 10.1021/acsmacrolett.7b00842
7. [7]
  P.C. Nicolson, J. Vogt, Biomaterials 22 (2001) 3273-3283. doi: 10.1016/S0142-9612(01)00165-X
8. [8]
  W.R. Dunnavant, R.A. Markle, P.B. Stickney, J.E. Curry, J.D. Byrd, J. Polym. Sci. Part A 5 (1967) 707-724. doi: 10.1002/pol.1967.150050402
9. [9]
  M. Wang, Q. Zhang, K.L. Wooley, Biomacromolecules 2 (2001) 1206-1213. doi: 10.1021/bm010093s
10. [10]
  Y. Li, Y. Kawakami, Des. Monomers Polym. 3 (2000) 399-419. doi: 10.1163/156855500750206357
11. [11]
  T. Nishikubo, A. Kameyama, Y. Kimura, K. Fukuyo, Macromolecules 28 (1995) 4361-4365. doi: 10.1021/ma00117a002
12. [12]
  S. Minegishi, M. Ito, T. Nishikubo, A. Kameyama, J. Polym. Sci. Part A Polym. Chem. 38 (2000) 2254-2259.
13. [13]
  T. Nishikubo, A. Kameyama, Y. Kimura, T. Nakamura, Macromolecules 29 (1996) 5529-5534. doi: 10.1021/ma960304z
14. [14]
  E. Sahmetlioglu, H.T.H. Nguyen, O. Nsengiyumva, E. Gokturk, S.A. Miller, ACS Macro Lett. 5 (2016) 466-470. doi: 10.1021/acsmacrolett.6b00095
15. [15]
  C. Cheng, A. Watts, M.A. Hillmyer, J.F. Hartwig, Angew. Chem. Int. Ed. 55 (2016) 11872-11876. doi: 10.1002/anie.201606282
16. [16]
  W.R. Dunnavant, R.A. Markle, R.G. Sinclair, et al., Macromolecules 1 (1968) 249-254. doi: 10.1021/ma60003a010
17. [17]
  M. Padmanaban, M.A. Kakimoto, Y. Imai, J. Polym. Sci. Part A Polym. Chem. 28 (1990) 2997-3005. doi: 10.1002/pola.1990.080281109
18. [18]
  C.S. Sample, S.H. Lee, M.W. Bates, et al., Macromolecules 52 (2019) 1993-1999. doi: 10.1021/acs.macromol.8b02741
19. [19]
  C. Li, L. Wang, M. Wang, et al., Angew. Chem. Int. Ed. 58 (2019) 11434-11438. doi: 10.1002/anie.201903800
20. [20]
  J.K. Paulasaari, W.P. Weber, Macromolecules 31 (1998) 7105-7107. doi: 10.1021/ma980795i
21. [21]
  G. Lázaro, M. Iglesias, F.J. Fernández-Alvarez, et al., ChemCatChem 5 (2013) 1133-1141. doi: 10.1002/cctc.201200309
22. [22]
  C. Li, X. Hua, Z. Mou, X. Liu, D. Cui, Macromol. Rapid Commun. 38 (2017) 1700590. doi: 10.1002/marc.201700590
23. [23]
  G. Lázaro, F.J. Fernández-Alvarez, M. Iglesias, et al., Catal. Sci. Technol. 4 (2014) 62-70. doi: 10.1039/C3CY00598D
24. [24]
  Y. Li, Y. Kawakami, Macromolecules 32 (1999) 8768-8773. doi: 10.1021/ma991312t
25. [25]
  T. Kawakita, H.S. Oh, J.Y. Moon, et al., Polym. Int. 50 (2001) 1346-1351. doi: 10.1002/pi.784
26. [26]
  Y. Li, Y. Kawakami, Macromolecules 32 (1999) 3540-3542. doi: 10.1021/ma9819743
27. [27]
  Y. Li, Y. Kawakami, Macromolecules 32 (1999) 6871-6873. doi: 10.1021/ma990511+
28. [28]
  R. Zhang, J.E. Mark, A.R. Pinhas, Macromolecules 33 (2000) 3508-3510. doi: 10.1021/ma000054t
29. [29]
  M. Oishi, J.Y. Moon, W. Janvikul, Y. Kawakami, Polym. Int. 50 (2001) 135-143. doi: 10.1002/1097-0126(200101)50:1<135::AID-PI600>3.0.CO;2-6
30. [30]
  Y. Li, M. Seino, Y. Kawakami, Macromolecules 33 (2000) 5311-5314. doi: 10.1021/ma992143f
31. [31]
  X.Y. Zhai, S.B. Hu, L. Shi, Y.G. Zhou, Organometallics 37 (2018) 2342-2347. doi: 10.1021/acs.organomet.8b00316
32. [32]
  X.Y. Zhai, X.Q. Wang, Y.X. Ding, Y.G. Zhou, Chin. Chem. Lett. 31 (2020) 1197-1200. doi: 10.1016/j.cclet.2019.07.017
33. [33]
  S. Vijjamarri, V.K. Chidara, G. Du, ACS Omega 2 (2017) 582-591. doi: 10.1021/acsomega.6b00538
34. [34]
  C. Lichtenberg, L. Viciu, M. Adelhardt, et al., Angew. Chem. Int. Ed. 54 (2015) 5766-5771. doi: 10.1002/anie.201411365
35. [35]
  C. Deutsch, N. Krause, B.H. Lipshutz, Chem. Rev. 108 (2008) 2916-2927. doi: 10.1021/cr0684321
36. [36]
  H. Ito, A. Watanabe, M. Sawamura, Org. Lett. 7 (2005) 1869-1871. doi: 10.1021/ol050559+
37. [37]
  S. Rendler, G. Auer, M. Oestreich, Angew. Chem. Int. Ed. 44 (2005) 7620-7624. doi: 10.1002/anie.200502631
38. [38]
  J. Seliger, X. Dong, M. Oestreich, Angew. Chem. Int. Ed. 58 (2019) 1970-1974. doi: 10.1002/anie.201813229
39. [39]
  X.Y. Zhai, X.Q. Wang, Y.G. Zhou, Eur. Polym. J. 134 (2020) 109832. doi: 10.1016/j.eurpolymj.2020.109832
40. [40]
  X.Q. Wang, X.Y. Zhai, B. Wu, Y.Q. Bai, Y.G. Zhou, ACS Macro Lett. 9 (2020) 969-973. doi: 10.1021/acsmacrolett.0c00225
41. [41]
  H. Mutlu, M.A.R. Meier, Eur. J. Lipid Sci. Technol. 112 (2010) 10-30. doi: 10.1002/ejlt.200900138
1. [1]
  Yi Herng Chan , Zhe Phak Chan , Serene Sow Mun Lock , Chung Loong Yiin , Shin Ying Foong , Mee Kee Wong , Muhammad Anwar Ishak , Ven Chian Quek , Shengbo Ge , Su Shiung Lam . Thermal pyrolysis conversion of methane to hydrogen (H₂): A review on process parameters, reaction kinetics and techno-economic analysis. Chinese Chemical Letters, 2024, 35(8): 109329-. doi: 10.1016/j.cclet.2023.109329
2. [2]
  Xiangyang Ji , Yishuang Chen , Peng Zhang , Shaojia Song , Jian Liu , Weiyu Song . Boosting the first C–H bond activation of propane on rod-like V/CeO₂ catalyst by photo-assisted thermal catalysis. Chinese Chemical Letters, 2025, 36(5): 110719-. doi: 10.1016/j.cclet.2024.110719
3. [3]
  Guizhi Zhu , Junrui Tan , Longfei Tan , Qiong Wu , Xiangling Ren , Changhui Fu , Zhihui Chen , Xianwei Meng . Growth of CeCo-MOF in dendritic mesoporous organosilica as highly efficient antioxidant for enhanced thermal stability of silicone rubber. Chinese Chemical Letters, 2025, 36(1): 109669-. doi: 10.1016/j.cclet.2024.109669
4. [4]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
5. [5]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
6. [6]
  Lin Zhang , Chaoran Li , Thongthai Witoon , Xingda An , Le He . Nano-thermometry in photothermal catalysis. Chinese Journal of Structural Chemistry, 2025, 44(4): 100456-100456. doi: 10.1016/j.cjsc.2024.100456
7. [7]
  Huakang Zong , Xinyue Li , Yanlin Zhang , Faxun Wang , Xingxing Yu , Guotao Duan , Yuanyuan Luo . Pt/Ti₃C₂ electrode material used for H₂S sensor with low detection limit and high stability. Chinese Chemical Letters, 2025, 36(5): 110195-. doi: 10.1016/j.cclet.2024.110195
8. [8]
  Kunpeng Zhou , Zhihao Shi , Xiao-Hong Yi , Peng Wang , Aiqun Li , Chong-Chen Wang . MOFs helping heritage against environmental threats. Chinese Chemical Letters, 2025, 36(5): 110226-. doi: 10.1016/j.cclet.2024.110226
9. [9]
  Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737
10. [10]
  Tong Tong , Lezong Chen , Siying Wu , Zhong Cao , Yuanbin Song , Jun Wu . Establishment of a leucine-based poly(ester amide)s library with self-anticancer effect as nano-drug carrier for colorectal cancer treatment. Chinese Chemical Letters, 2024, 35(12): 109689-. doi: 10.1016/j.cclet.2024.109689
11. [11]
  Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
12. [12]
  Jiaqi Jia , Kathiravan Murugesan , Chen Zhu , Huifeng Yue , Shao-Chi Lee , Magnus Rueping . Multiphoton photoredox catalysis enables selective hydrodefluorinations. Chinese Chemical Letters, 2025, 36(2): 109866-. doi: 10.1016/j.cclet.2024.109866
13. [13]
  Ning LI , Siyu DU , Xueyi WANG , Hui YANG , Tao ZHOU , Zhimin GUAN , Peng FEI , Hongfang MA , Shang JIANG . Preparation and efficient catalysis for olefins epoxidation of a polyoxovanadate-based hybrid. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 799-808. doi: 10.11862/CJIC.20230372
14. [14]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
15. [15]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
16. [16]
  Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579
17. [17]
  Xiao Xiao , Biao Chen , Jia-Wei Li , Jun-Bo Zheng , Xu Wang , Hang Zhao , Fen-Er Chen . Nitrite-catalyzed economic and sustainable bromocyclization of tryptamines/tryptophols to access hexahydropyrrolo[2,3-b]indoles/tetrahydrofuroindolines in batch and flow. Chinese Chemical Letters, 2024, 35(7): 109280-. doi: 10.1016/j.cclet.2023.109280
18. [18]
  Haojie Song , Laiyu Luo , Siyu Wang , Guo Zhang , Baojiang Jiang . Advances in poly(heptazine imide)/poly(triazine imide) photocatalyst. Chinese Chemical Letters, 2024, 35(10): 109347-. doi: 10.1016/j.cclet.2023.109347
19. [19]
  Yuqing Liu , Yu Yang , Yuhan E , Changlong Pang , Di Cui , Ang Li . Insight into microbial synthesis of metal nanomaterials and their environmental applications: Exploration for enhanced controllable synthesis. Chinese Chemical Letters, 2024, 35(11): 109651-. doi: 10.1016/j.cclet.2024.109651
20. [20]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(656)
HTML views(45)

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