双亲性光敏感遥爪聚合物C-PNIPAAm的合成与性能

doi:10.3866/PKU.WHXB20100929

Abstract

Abstract:

Coumarin-containing disulfide (C-S-S-C) was designed and synthesized, which could be used as chain transfer agent with tributylphosphine and water. With N-isopropyl acrylamide (NIPAAm) as monomer and azodiiso- butyronitrile (AIBN) as initiator, an amphiphilic photosensitive telechelic polymer (C-PNIPAAm) was synthesized. The polymer was characterized by Fourier transform infrared (FT-IR) spectroscopy, gel permeation chromatography (GPC) and proton nuclear magnetic resonance spectroscopy (¹H-NMR). We found that the polymer can form micelles in water itself with fluorescein as a hydrophobic agent. When irradiated by UV light (λ>310 nm), the coumarin unit at the end of the polymer chain was photodimerized, which changed the micelle structure and hydrophobic fluorescein was effectively released to the water. Dynamic laser scattering (DLS) showed that the average diameter of the micelles increased from56.6 nmto 101.0 nmafter irradiation.

Key words: Coumarin, Poly N-isopropyl acrylamide, Fluorescein, Photo-dimerization, Amphiphilic

SHU Qiao-Zhen, CHEN Xin, CHEN Kai-Hua, JIANG Jin-Qiang, NI Zhong-Bin, ZHANG Hong-Wu, LIU Xiao-Ya, CHEN Ming-Qing. Synthesis and Properties of Amphiphilic Photosensitive Telechelic Polymer C-PNIPAAm[J]. Acta Phys. -Chim. Sin. 2010, 26(10), 2845-2850. doi: 10.3866/PKU.WHXB20100929

References

1. Gao, J.; He, Y. N.; Liu, F.; Zhang, X.; Wang, Z. Q.;Wang, X. G. Chem. Mater., 2007, 19(16): 3877
2. Goodwin, A. P.; Mynar, J. L.; Ma, Y. Z.; Fleming, G. R.; Fréchet, J. M. J. J. Am. Chem. Soc., 2005, 127: 9952
3. Liu, G. J.; Zhou, J. Y. Macromolecules, 2002, 35(21): 8167
4. Xi, C. H.; Liu, X. Y.; Chen, M. Q.; Yang, C. Journal of Jiangnan University: Natural Science Edition, 2005, 4(2): 195 [奚朝晖, 刘晓亚,陈明清,杨成. 江南大学学报:自然科学版, 2005, 4(2): 195]
5. Shi, D. J.; Liu, X. Y.; Chen, M. Q.; Yang, C.; Gu, Z. B.; Xiang, F. Acta Polymerica Sinica, 2004: 600 [施冬健, 刘晓亚,陈明清, 杨成, 顾正彪,相飞.高分子学报, 2004: 600]
6. Njikang, G.; Liu, G. J.; Scott, A.; Curda, S. A. Macromolecules, 2008, 41(15): 5697
7. Trenor, S. R.; Shultz, A. R.; Love, B. J.; Long, T. E. Chem. Rev., 2004, 104: 3059
8. Kim, C.; Trajkovska, A.; Wallace, J. U.; Chen, S. H. Macromolecules, 2006, 39(11): 3817
9. Zhao, D. L.; Ren, B. Y.; Liu, S. S.; Liu, X. X.; Tong, Z. Chem. Commun., 2006: 779
10. Ren, B. Y.; Zhao, D .L.; Liu, S, S.; Liu, X. X.; Tong, Z. Macromolecules, 2007, 40(13): 4501
11. Kim, C.; Wallace, J. U.; Trajkovska, A.; Ou, J. J.; Chen, S. H. Macromolecules, 2007, 40(25): 8924
12. Jiang, J. Q.; Feng, Y.; Wang, H. M.; Liu, X. Y.; Zhang, S.W.; Chen, M. Q. Acta Phys. -Chim. Sin., 2008, 24(11): 2089 [江金强,冯艳,王红梅, 刘晓亚,张胜文,陈明清. 物理化学学报, 2008, 24(11): 2089]
13. Jiang, J. Q.; Qi, B.; Lepage, M.; Zhao, Y. Macromolecules, 2007, 40(4): 790
14. Fu, Q.; Cheng, L. L.; Zhang, Y.; Shi, W. F. Polymer, 2008, 49: 4981
15. Fu, Q. The synthesis and functionalization of hyperbranched polyesters and their photosensitive properties [D]. Hefei: UniVersity of Seience and Technology of China, 2009 [傅祺. 超支化聚酯的合成与表面修饰及其光敏性能研究[D].合肥: 中国科学技术大学, 2009]
16. Zhao, Y.; Bertrand, J.; Tong, X.; Zhao, Y. Langmuir, 2009, 25 (22): 13151
17. Babin, J.; Lepage, M.; Zhao, Y. Macromolecules, 2008, 41(4): 1246
18. He, J.; Tong, X.; Zhao, Y. Macromolecules, 2009, 42(13): 4845
19. He, J.; Zhao, Y.; Zhao, Y. Soft Matter., 2009, 5: 308
20. Zhang, C. Z.; Jiang, C. X.; Wang, X.; Chen, D. B.; Zhong, A. Y. Polymer Materials Science and Engineering, 2007, 23(6): 85 [张传智, 蒋春霞,王旭,陈德本,钟安永. 高分子材料科学与工程, 2007, 23(6): 85]
21. Jiang, J. Q.; Tong, X.; Zhao, Y. J. Am. Chem. Soc., 2005, 127: 8290
22. Jiang, J. Q.; Tong, X.; Morris, D.; Zhao, Y. Macromolecules, 2006, 39(13): 4633
23. Humphrey, R. E.; Hawkins, J. M. Analytical Chemistry, 1964, 36 (9): 1812
24. Humphrey, R. E.; Hawkins, J. M. Analytical Chemistry, 1965, 37 (1): 164
25. Tsarevsky, N. V.; Matyjaszewski, K. Macromolecules, 2005, 38 (8): 3087
26. Yang, J. H.; Ji, C. B.; Zhao, Y. M. Chinese Journal of Organic Chemistry, 2008, 28(10): 1740 [杨金会,计从斌,赵艳敏.有机化学, 2008, 28(10): 1740]
27. Sonavane, S. U.; Chidambaram, M.; Khalil, S.; Almog, J.; Sasson, Y. Tetrahedron Letters, 2008, 49: 520

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Synthesis and Properties of Amphiphilic Photosensitive Telechelic Polymer C-PNIPAAm

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