Citation: Lilong Gao, Yuhao Zhai, Dongdong Zhang, Linjun Huang, Kunyan Sui. Exploration of Thiol-Ene Click Polymerization in Polymer Chemistry Experiment Teaching[J]. University Chemistry, ;2025, 40(4): 87-93. doi: 10.12461/PKU.DXHX202405143 shu

Exploration of Thiol-Ene Click Polymerization in Polymer Chemistry Experiment Teaching

College of Materials Science and Engineering, Qingdao University, Qingdao 266071, Shandong Province, China

Received Date: 20 May 2024
Revised Date: 14 August 2024

The addition reaction between thiols and vinyl ethers is an anti-Markovnikov addition reaction based on a free radical mechanism, which proceeds efficiently under ultraviolet (UV) irradiation in the presence of photoinitiator or photosensitizer. In this experiment, triethylene glycol divinyl ether (TEGDVE) and 3,6-dioxa-1,8-octanedithiol (DODT) were selected as monomers to synthesize poly(ether-thioether) polymers through thiol-ene click stepwise polymerization. Nuclear magnetic resonance (NMR) was used to determine the molecular structure of the polymers, and gel permeation chromatography (GPC) was employed to measure the molecular weight of the obtained polymers. Strategies to achieve high-molecular-weight polyaddition products were explored by adjusting the molar ratio of monomers and polymerization time. The mechanism of the polymerization reaction was further verified by introducing radical scavengers. This experiment serves as a simple, efficient, green, and environmentally friendly comprehensive polymer chemistry experiment.
- Thiol-ene click reaction,
- Dithiol and divinyl ether,
- Stepwise polymerization,
- Molecular weight control method,
- Gel permeation chromatography
1. [1]
  Baekeland, L. H. J. Ind. Eng. Chem. US 1909, 1, 149.
2. [2]
  Staudinger, H. Ber. Dtsch. Chem. Ges. 1920, 53, 1073.
3. [3]
  Blasco, E.; Sims, M. B.; Goldmann, A. S.; Sumerlin, B. S.; Barner-Kowollik, C. Macromolecules 2017, 50 (14), 5215.
4. [4]
  Barner-Kowollik, C.; Du Prez, F. E.; Espeel, P.; Hawker, C. J.; Junkers, T.; Schlaad, H.; Van Camp, W. Angew. Chem. Int. Ed. 2011, 50 (1), 60.
5. [5]
  Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40 (11), 2004.
6. [6]
  Song, Q.; Li, F.; Tan, X.; Yang, L.; Wang, Z.; Zhang, X. Polym. Chem. 2014, 5 (20), 5895.
7. [7]
8. [8]
9. [9]
10. [10]
11. [11]
12. [12]
13. [13]
  Gao, L.; Li, X.; Wang, Y.; Zhu, W.; Shen, Z.; Li, X. J. Polym. Sci., Part A: Polym. Chem. 2016, 54 (17), 2651.
14. [14]
  Zhu, W.; Gao, L.; Luo, Q.; Gao, C.; Zha, G.; Shen, Z.; Li, X. Polym. Chem. 2014, 5 (6), 2018.
15. [15]
  Gregory, A.; Stenzel, M. H. Prog. Polym. Sci. 2012, 37 (1), 38.
16. [16]
  Such, G. K.; Johnston, A. P. R.; Liang, K.; Caruso, F. Prog. Polym. Sci. 2012, 37 (7), 985.
17. [17]
  Yang, W. J.; Neoh, K.-G.; Kang, E.-T.; Teo, S. L.-M.; Rittschof, D. Prog. Polym. Sci. 2014, 39 (5), 1017.
18. [18]
  Hayashi, M.; Katayama, A. ACS Appl. Polym. Mater. 2020, 2 (6), 2452.
19. [19]
  Lyon, G. B.; Cox, L. M.; Goodrich, J. T.; Baranek, A. D.; Ding, Y.; Bowman, C. N. Macromolecules 2016, 49 (23), 8905.
20. [20]
  The Nobel Prize in Chemistry 2022. [2025-02-12]. https://www.nobelprize.org/prizes/chemistry/2022/summary/
21. [21]
  Lowe, A. B. Polym. Chem. 2010, 1 (1), 17.
1. [1]
  Xiaoli Sun , Xiang Wu , Li Gan , Wenming Wan . Barbier Polymerization: A New Teaching Case for Step-Growth Polymerization. University Chemistry, 2025, 40(4): 113-118. doi: 10.12461/PKU.DXHX202406102
2. [2]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
3. [3]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
4. [4]
  Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
5. [5]
  Pingping Zhu , Qiang Zhou , Yu Huang , Haiyang Yang , Pingsheng He , Shiyan Xiao . Design and Practice of Ideological and Political Cases in the Course of Polymer Physics Experiments: Molecular Weight Determination of Polymers by Dilute Solution Viscosity Method as an Example. University Chemistry, 2025, 40(4): 94-99. doi: 10.12461/PKU.DXHX202405170
6. [6]
  Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
7. [7]
  Zhaoxuan ZHU , Lixin WANG , Xiaoning TANG , Long LI , Yan SHI , Jiaojing SHAO . Application of poly(vinyl alcohol) conductive hydrogel electrolytes in zinc ion batteries. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 893-902. doi: 10.11862/CJIC.20240368
8. [8]
  Yiping HUANG , Liqin TANG , Yufan JI , Cheng CHEN , Shuangtao LI , Jingjing HUANG , Xuechao GAO , Xuehong GU . Hollow fiber NaA zeolite membrane for deep dehydration of ethanol solvent by vapor permeation. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 225-234. doi: 10.11862/CJIC.20240224
9. [9]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
10. [10]
  Jiajia Li , Xiangyu Zhang , Zhihan Yuan , Zhengyang Qian , Jian Zhu . 3D Printing Based on Photo-Induced Reversible Addition-Fragmentation Chain Transfer Polymerization. University Chemistry, 2024, 39(5): 11-19. doi: 10.3866/PKU.DXHX202309073
11. [11]
  Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
12. [12]
  .
  南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积
  . CCS Chemistry, 2025, 7(0): -.
13. [13]
  Zeyi Yan , Ruitao Liu , Xinyu Qi , Yuxiang Zhang , Lulu Sun , Xiangyuan Li , Anchao Feng . Exploration of Suspension Polymerization: Preparation and Fluorescence Stability of Perovskite Polystyrene Microbeads. University Chemistry, 2025, 40(4): 72-79. doi: 10.12461/PKU.DXHX202405110
14. [14]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
15. [15]
  Fanpeng Meng , Fei Zhao , Jingkai Lin , Jinsheng Zhao , Huayang Zhang , Shaobin Wang . 优化氮化碳纳米片/球形共轭聚合物S型异质结界面电场以促进析氢反应. Acta Physico-Chimica Sinica, 2025, 41(8): 100095-. doi: 10.1016/j.actphy.2025.100095
16. [16]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
17. [17]
  Dongdong Yao , JunweiGu , Yi Yan , Junliang Zhang , Yaping Zheng . Teaching Phase Separation Mechanism in Polymer Blends Using Process Representation Teaching Method: A Teaching Design for Challenging Theoretical Concepts in “Polymer Structure and Properties” Course. University Chemistry, 2025, 40(4): 131-137. doi: 10.12461/PKU.DXHX202408125
18. [18]
  Tengjiao Wang , Tian Cheng , Rongjun Liu , Zeyi Wang , Yuxuan Qiao , An Wang , Peng Li . Conductive Hydrogel-based Flexible Electronic System: Innovative Experimental Design in Flexible Electronics. University Chemistry, 2024, 39(4): 286-295. doi: 10.3866/PKU.DXHX202309094
19. [19]
  Yuting Zhang , Zhiqian Wang . Methods and Case Studies for In-Depth Learning of the Aldol Reaction Based on Its Reversible Nature. University Chemistry, 2024, 39(7): 377-380. doi: 10.3866/PKU.DXHX202311037
20. [20]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(547)
HTML views(50)

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

Exploration of Thiol-Ene Click Polymerization in Polymer Chemistry Experiment Teaching

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

Metrics

通讯作者: 陈斌, bchen63@163.com