Citation: Zhen Lu, Bogeng Guo, Yulai Zhao, Linxi Hou, Longqiang Xiao. One-step synthesis of cyclic polypyrazole and the self-assembly vesicles driven by hydrogen bond[J]. Chinese Chemical Letters, ;2022, 33(2): 825-829. doi: 10.1016/j.cclet.2021.07.033 shu

One-step synthesis of cyclic polypyrazole and the self-assembly vesicles driven by hydrogen bond

Zhen Lu ^{a, b, 1} ,
Bogeng Guo ^{a, 1} ,
Yulai Zhao ^{a, b} ,
Linxi Hou ^{a, b, *} ,
Longqiang Xiao ^{a, b, *}

a.
Department of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Fuzhou University, Fuzhou 350116, China
b.
Fujian Key Laboratory of Advanced Manufacturing Technology of Specialty Chemicals, Fuzhou University, Fuzhou 350116, China

lxhou@fzu.edu.cn

xiaolq@fzu.edu.cn

Received Date: 11 May 2021
Revised Date: 5 July 2021
Accepted Date: 8 July 2021
Available Online: 15 July 2021

Figures(6)

The synthesis of cyclic polymer is an important topic in polymer chemistry. Herein, we report a one-step method to prepare cyclic polypyrazoles. Monomers with two functional groups, diazo and alkyne, were synthesized and polymerized via 1,3-diploar cycloaddition in bulk under heating without any catalyst. Polypyrazoles with molecular weights in the range of 3800-4400 g/mol and yields in the range of 78.8-98.7% were successfully synthesized. No chain end group was detected by LC-QTOF-MS and FTIR, which proves the cyclic structure of polypyrazoles. What is noteworthy is that the cyclic polypyrazoles can self-assemble into vesicles during the reprecipitation process, which was proved by the results of SEM and TEM. The reason for that is the formation of intermolecular hydrogen bond between NH and ester groups.
- 1,3-Dipolar cycloaddition,
- Polypyrazole,
- Self-assembly,
- Cyclic polymers
1. [1]
  S. Zhang, X. Cheng, J. Wang, et al., Polym. Chem. 9(2018) 5155-5163. doi: 10.1039/C8PY01014E
2. [2]
  W. Ryu, L. Xiang, T. Jeon, M. Ree, Polymer 207(2020) 122899. doi: 10.1016/j.polymer.2020.122899
3. [3]
  J. Chen, H. Li, H. Zhang, et al., Nat. Commun. 9(2018) 5310. doi: 10.1038/s41467-018-07754-1
4. [4]
  Z. Liu, Y. Huang, X. Zhang, et al., Macromolecules 51(2018) 7672-7679. doi: 10.1021/acs.macromol.8b00950
5. [5]
  Y. Jiang, Z. Zhang, D. Wang, N. Hadjichristidis, Macromolecules 51(2018) 3193-3202. doi: 10.1021/acs.macromol.8b00333
6. [6]
  L. Guo, D. Zhang, J. Am. Chem. Soc. 131(2009) 18072-18074. doi: 10.1021/ja907380d
7. [7]
  D. Tan, X. Hu, Z. Cao, M. Luo, D.J. Darensbourg, ACS Macro Lett. 9(2020) 866-871. doi: 10.1021/acsmacrolett.0c00302
8. [8]
  Y. Cai, J. Lu, F. Zhou, et al., Macromol. Rapid Commun. 35(2014) 901-907. doi: 10.1002/marc.201300913
9. [9]
  S. Zhang, Y. Tezuka, Z. Zhang, et al., Polym. Chem. 9(2018) 677-686. doi: 10.1039/C7PY01544E
10. [10]
  W. Zhu, Z. Li, Y. Zhao, K. Zhang, Macromol. Rapid Commun. 36(2015) 1987-1993. doi: 10.1002/marc.201500367
11. [11]
  T.E. Gartner Ⅲ, F.M. Haque, A.M. Gomi, et al., Macromolecules 52(2019) 4579-4589. doi: 10.1021/acs.macromol.9b00600
12. [12]
  Y. Jeong, Y. Jin, T. Chang, F. Uhlik, J. Roovers, Macromolecules 50(2017) 7770-7776. doi: 10.1021/acs.macromol.7b01511
13. [13]
  Z. Jia, M.J. Monteiro, J. Polym. Sci. Part A: Polym. Chem. 50(2012) 2085-2097. doi: 10.1002/pola.25999
14. [14]
  L. Gao, J. Oh, Y. Tu, T. Chang, C.Y. Li, Polymer 170(2019) 198-203. doi: 10.1016/j.polymer.2019.03.018
15. [15]
  M.A. Cortez, W.T. Godbey, Y. Fang, et al., J. Am. Chem. Soc. 137(2015) 6541-6549. doi: 10.1021/jacs.5b00980
16. [16]
  G. Kang, L. Sun, Y. Liu, et al., Langmuir 35(2019) 12509-12517. doi: 10.1021/acs.langmuir.9b02346
17. [17]
  X.Y. Tu, M.Z. Liu, H. Wei, J. Polym. Sci. Part A: Polym. Chem. 54(2016) 1447-1458. doi: 10.1002/pola.28051
18. [18]
  T. Josse, J. De Winter, P. Gerbaux, O. Coulembier, Angew. Chem. Int. Ed. 55(2016) 13944-13958. doi: 10.1002/anie.201601677
19. [19]
  F.M. Haque, S.M. Grayson, Nat. Chem. 12(2020) 433-444. doi: 10.1038/s41557-020-0440-5
20. [20]
  P. Sun, J.A. Liu, Z. Zhang, K. Zhang, Polym. Chem. 7(2016) 2239-2244. doi: 10.1039/C6PY00165C
21. [21]
  H. Zhang, W. Wu, X. Zhao, Y. Zhao, Macromolecules 50(2017) 3411-3423. doi: 10.1021/acs.macromol.7b00220
22. [22]
  B.A. Laurent, S.M. Grayson, Chem. Soc. Rev. 38(2009) 2202-2213. doi: 10.1039/b809916m
23. [23]
  M.W. Ali, Z. Muhammad, Q. Jia, et al., Polym. Chem. 11(2020) 4164-4171. doi: 10.1039/D0PY00599A
24. [24]
  T. He, G.H. Zheng, C.Y. Pan, Macromolecules 36(2003) 5960-5966. doi: 10.1021/ma021371y
25. [25]
  L. Gao, Z. Ji, Y. Zhao, et al., ACS Macro Lett. 8(2019) 1564-1569. doi: 10.1021/acsmacrolett.9b00747
26. [26]
  J.N. Hoskins, S.M. Grayson, Macromolecules 42(2009) 6406-6413. doi: 10.1021/ma9011076
27. [27]
  H. Wei, D.S.H. Chu, J. Zhao, J.A. Pahang, S.H. Pun, ACS Macro Lett. 2(2013) 1047-1050. doi: 10.1021/mz400560y
28. [28]
  X. Wan, T. Liu, S. Liu, Biomacromolecules 12(2011) 1146-1154. doi: 10.1021/bm101463d
29. [29]
  M. Cai, J. Hu, J.L. Tian, et al., Chin. Chem. Lett. 26(2015) 675-680. doi: 10.1016/j.cclet.2015.03.015
30. [30]
  J.C. Chen, Y.P. Wang, H.D. Wang, et al., Chin. Chem. Lett. 21(2010) 496-500. doi: 10.1016/j.cclet.2009.11.025
31. [31]
  Y. Oga, Y. Hosoi, A. Takasu, Polymer 186(2020) 122019. doi: 10.1016/j.polymer.2019.122019
32. [32]
  Y.A. Chang, R.M. Waymouth, J. Polym. Sci. Part A: Polym. Chem. 55(2017) 2892-2902. doi: 10.1002/pola.28635
33. [33]
  S. Lv, Y. Sun, Y. Xu, S. Yang, L. Wang, Chin. Chem. Lett. 31(2020) 1568-1571. doi: 10.1016/j.cclet.2019.11.027
34. [34]
  C.W. Bielawski, D. Benitez, R.H. Grubbs, Science 297(2002) 2041-2044. doi: 10.1126/science.1075401
35. [35]
  S.A. Gonsales, T. Kubo, M.K. Flint, et al., J. Am. Chem. Soc. 138(2016) 4996-4999. doi: 10.1021/jacs.6b00014
36. [36]
  A. Bunha, P.F. Cao, J.D. Mangadlao, R.C. Advincula, React. Funct. Polym. 80(2014) 33-39. doi: 10.1016/j.reactfunctpolym.2014.03.001
37. [37]
  K. Zhang, M.A. Lackey, Y. Wu, G.N. Tew, J. Am. Chem. Soc. 133(2011) 6906-6909. doi: 10.1021/ja2007559
38. [38]
  E.J. Shin, H.A. Brown, S. Gonzalez, et al., Angew. Chem. Int. Ed. 50(2011) 6388-6391. doi: 10.1002/anie.201101853
39. [39]
  H.A. Brown, Y.A. Chang, R.M. Waymouth, J. Am. Chem. Soc. 135(2013) 18738-18741. doi: 10.1021/ja409843v
40. [40]
  L. Xiao, S. Cai, Q. Liu, et al., Polym. Chem. 5(2014) 607-613. doi: 10.1039/C3PY01105D
41. [41]
  T. Toma, J. Shimokawa, T. Fukuyama, Org. Lett. 9(2007) 3195-3197. doi: 10.1021/ol701432k
42. [42]
  F. Sanda, T. Kawano, T. Masuda, Polym. Bull. 55(2005) 341-347. doi: 10.1007/s00289-005-0445-7
43. [43]
  S. Wang, B. Cheng, Sci. Rep. 7(2017) 12712. doi: 10.1038/s41598-017-12727-3
44. [44]
  M.R. Bhosle, L.D. Khillare, S.T. Dhumal, R.A. Mane, Chin. Chem. Lett. 27(2016) 370-374. doi: 10.1016/j.cclet.2015.12.005
45. [45]
  X. Tang, C. Zheng, Y. Chen, et al., Macromolecules 49(2016) 9291-9300. doi: 10.1021/acs.macromol.6b02192
46. [46]
  C. Chen, C.G. Wang, L. Xiao, A. Goto, Chem. Commun. 54(2018) 13738-13741. doi: 10.1039/C8CC08157C
47. [47]
  G. Feng, S. Xu, R. Chen, et al., Tetrahedron Lett. 61(2020) 152622. doi: 10.1016/j.tetlet.2020.152622
48. [48]
  L.L. Bengel, B. Aberle, A.N. Egler-Kemmerer, et al., Angew. Chem. Int. Ed. 60(2020) 5554-5560. doi: 10.1002/anie.201914775
49. [49]
  J.P. Castaneda, G.S. Denisov, S.Y. Kucherov, V.M. Schreiber, A. Shurukhina, J. Mol. Struct. 660(2003) 25-40. doi: 10.1016/j.molstruc.2003.07.010
50. [50]
  Y. Cui, Z. Xu, H.Y. Li, et al., ACS Appl. Polym. Mater. 2(2020) 4512-4520. doi: 10.1021/acsapm.0c00592
51. [51]
  M.R. Ghadiri, J.R. Granja, R.A. Milligan, D.E. McRee, N. Khazanovich, Nature 366(1993) 324-327. doi: 10.1038/366324a0
1. [1]
  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
2. [2]
  Yuwen Zhu , Xiang Deng , Yan Wu , Baode Shen , Lingyu Hang , Yuye Xue , Hailong Yuan . Formation mechanism of herpetrione self-assembled nanoparticles based on pH-driven method. Chinese Chemical Letters, 2025, 36(1): 109733-. doi: 10.1016/j.cclet.2024.109733
3. [3]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
4. [4]
  Jingqi Xin , Shupeng Han , Meichen Zheng , Chenfeng Xu , Zhongxi Huang , Bin Wang , Changmin Yu , Feifei An , Yu Ren . A nitroreductase-responsive nanoprobe with homogeneous composition and high loading for preoperative non-invasive tumor imaging and intraoperative guidance. Chinese Chemical Letters, 2024, 35(7): 109165-. doi: 10.1016/j.cclet.2023.109165
5. [5]
  Keyang Li , Yanan Wang , Yatao Xu , Guohua Shi , Sixian Wei , Xue Zhang , Baomei Zhang , Qiang Jia , Huanhua Xu , Liangmin Yu , Jun Wu , Zhiyu He . Flash nanocomplexation (FNC): A new microvolume mixing method for nanomedicine formulation. Chinese Chemical Letters, 2024, 35(10): 109511-. doi: 10.1016/j.cclet.2024.109511
6. [6]
  Xuanyu Wang , Zhao Gao , Wei Tian . Supramolecular confinement effect enabling light-harvesting system for photocatalytic α-oxyamination reaction. Chinese Chemical Letters, 2024, 35(11): 109757-. doi: 10.1016/j.cclet.2024.109757
7. [7]
  Xian Yan , Huawei Xie , Gao Wu , Fang-Xing Xiao . Boosted solar water oxidation steered by atomically precise alloy nanocluster. Chinese Chemical Letters, 2025, 36(1): 110279-. doi: 10.1016/j.cclet.2024.110279
8. [8]
  Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
9. [9]
  Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
10. [10]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
11. [11]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
12. [12]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
13. [13]
  Ruoxi Sun , Yiqian Xu , Shaoru Rong , Chunmiao Han , Hui Xu . The Enchanting Collision of Light and Time Magic: Exploring the Footprints of Long Afterglow Lifetime. University Chemistry, 2024, 39(5): 90-97. doi: 10.3866/PKU.DXHX202310001
14. [14]
  Yi Liu , Peng Lei , Yang Feng , Shiwei Fu , Xiaoqing Liu , Siqi Zhang , Bin Tu , Chen Chen , Yifan Li , Lei Wang , Qing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571
15. [15]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
16. [16]
  Bing Niu , Honggao Huang , Liwei Luo , Li Zhang , Jianbo Tan . Coating colloidal particles with a well-defined polymer layer by surface-initiated photoinduced polymerization-induced self-assembly and the subsequent seeded polymerization. Chinese Chemical Letters, 2025, 36(2): 110431-. doi: 10.1016/j.cclet.2024.110431
17. [17]
  Yi Zhou , Wei Zhang , Rong Fu , Jiaxin Dong , Yuxuan Liu , Zihang Song , Han Han , Kang Cai . Self-assembly of two pairs of homochiral M₂L₄ coordination capsules with varied confined space using Tröger's base ligands. Chinese Chemical Letters, 2025, 36(2): 109865-. doi: 10.1016/j.cclet.2024.109865
18. [18]
  Xingwen Cheng , Haoran Ren , Jiangshan Luo . Boosting the self-trapped exciton emission in vacancy-ordered double perovskites via supramolecular assembly. Chinese Journal of Structural Chemistry, 2024, 43(6): 100306-100306. doi: 10.1016/j.cjsc.2024.100306
19. [19]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
20. [20]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(832)
HTML views(53)

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