Citation: Li Lingdong, Chi Xiaofang, Yan Jiawei, Zhao Zihan. Synthesis and Immobilization of Pyridinium N-Chloramine Precursors on PU Film for Antibacterial Application[J]. Chinese Journal of Organic Chemistry, ;2018, 38(4): 955-962. doi: 10.6023/cjoc201708056 shu

Synthesis and Immobilization of Pyridinium N-Chloramine Precursors on PU Film for Antibacterial Application

School of Petroleum and Chemical Engineering, Dalian University of Technology, Panjin 124221

Corresponding author: Li Lingdong, lild@dlut.edu.cn
Received Date: 27 August 2017
Revised Date: 28 November 2017
Available Online: 8 April 2017
Fund Project: the Fundamental Research Funds for the Central Universities DUT14RC(3)081Project supported by the Fundamental Research Funds for the Central Universities (Nos. DUT14RC(3)081, DUT17LK17) and the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministrythe Fundamental Research Funds for the Central Universities DUT17LK17

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In this work, two novel pyridinium N-chloramine precursors were designed and synthesized, both of which contain perfluorophenyl azide (PFPA) unit as the photo-coupling handle. The synthetic precursors were photo immobilized on commercial PU films upon UV (254 nm) light irradiation. After exposure to diluted household bleach, the resulting PU films were rendered biocidal. Antibacterial tests showed that satisfactory was achieved for both surface modified films and that the film grafted with shorter alkyl linker-contained precursor demonstrated even higher biocidal efficacy. Non-leaching antibacterial PU materials were herein developed based on PFPA-coupling strategy, providing a simple and universal method to confer N-chloramines on inert polymer surface for antibacterial application.
- pyridinium N-chloramine precursors,
- multi-step synthesis,
- fluorophenyl azide (PFPA) chemistry,
- biocidal polyurethane film,
- antimicrobial activity
1. [1]
  Kang, Z.; Jiao, Y.; Zhang, B.; Liang, J. J. Shanghai Normal Univ. (Nat. Sci. Ed.) 2012, 41, 540(in Chinese). doi: 10.3969/j.issn.1000-5137.2012.05.016
2. [2]
  Hui, F.; Debiemme-Chouvy, C. Biomacromolecules 2013, 14, 585. doi: 10.1021/bm301980q
3. [3]
  Dong, A.; Wang, Y.-J.; Gao, Y.; Gao, T.; Gao G. Chem. Rev. 2017, 117, 4806. doi: 10.1021/acs.chemrev.6b00687
4. [4]
  Gottardi, W.; Debabov, D.; Nagl, M. Antimicrob. Agents Chemother. 2013, 57, 1107. doi: 10.1128/AAC.02132-12
5. [5]
  Jie, Z.; Yan, X.; Zhao, L.; Worley, S. D.; Liang. J. RSC Adv. 2014, 4, 6048. doi: 10.1039/c3ra47147k
6. [6]
  Li, L.; Pu, T.; Zhanel, G.; Zhao, N.; Ens, W.; Liu, S. Adv. Healthcare Mater. 2012, 1, 609. doi: 10.1002/adhm.201200018
7. [7]
  Ning, C.; Li, L.; Logsetty, S.; Ghanbar, S.; Guo, M.; Ensf, W.; Liu, S. RSC Adv. 2015, 5, 93877. doi: 10.1039/C5RA15714E
8. [8]
  Li, L.; Zhao, Y.; Zhou, H.; Ning, A.; Zhang, F.; Zhao, Z. Tetrahedron Lett. 2017, 58, 321. doi: 10.1016/j.tetlet.2016.12.021
9. [9]
  Li, L.; Zhou, H.; Gai, F.; Chi, X.; Zhang, F.; ZhaoZ. RSC Adv. 2017, 7, 13244. doi: 10.1039/C6RA24954J
10. [10]
  Liang, J.; Chen, Y.; Ren, X. Ind. Eng. Chem. Res. 2007, 46, 6425. doi: 10.1021/ie0707568
11. [11]
  Wu, L.; Liu A.; Li, Z. Fibers Polym. 2015, 16, 550. doi: 10.1007/s12221-015-0550-7
12. [12]
  Sun, Y. Y.; Sun, G. J. Appl. Polym. Sci. 2001, 81, 1517. doi: 10.1002/(ISSN)1097-4628
13. [13]
  Liu, L.-H.; Yan, M. Acc. Chem. Res. 2010, 43, 1434. doi: 10.1021/ar100066t
14. [14]
  Li, L.; Li, J.; Kulkarni, A.; Liu, S. J. Mater. Chem., 2013, 1, 571. doi: 10.1039/C2TB00248E
15. [15]
  Williamson, M. R.; Black, R.; Kielty, C. Biomaterials 2006, 27, 3608.
16. [16]
  Li, L.; Chi, X.; Gai, F.; Zhou, H.; Zhang, F.; Zhao, Z. J. Appl. Polym. Sci. 2017, 134, 45323. doi: 10.1002/app.45323
17. [17]
  Dastgir, S.; Coleman, K. S.; Green, M. L. H. Dalton Trans. 2011, 40, 661. doi: 10.1039/C0DT00760A
18. [18]
  Keana, J. F. W.; Cai, S. X. J. Org. Chem. 1990, 55, 3640. doi: 10.1021/jo00298a048
19. [19]
  Xiong, J.; Xia, L.; Shentu, B.; Weng, Z. J. Appl. Polym. Sci. 2014, 131, 39812.
20. [20]
  Renaudie, L.; Narvor, C. L.; Lepleux, E.; Roger, P. Biomacromolecules 2007, 8, 679. doi: 10.1021/bm060961r
21. [21]
  Li, L.; Zhao, N.; Liu, S. Polymer 2012, 53, 67. doi: 10.1016/j.polymer.2011.11.036
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