Citation: Song Qiusheng, Zhou Wen, Wu Xinmin, Wu Fan. Dual Stimulus-responsive Fluorescence Behavior and Mechanism of P(NIPAM-co-RhBHA)-NP[J]. Acta Chimica Sinica, ;2016, 74(5): 435-440. doi: 10.6023/A16010073 shu

Dual Stimulus-responsive Fluorescence Behavior and Mechanism of P(NIPAM-co-RhBHA)-NP

1.
School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China

Corresponding author: Song Qiusheng, sqshfut@126.com
Received Date: 31 January 2016

Figures(12)

In the present study, based on spectral overlap between 1, 8-naphthalimide and N-acrylyl-N'-rhodamine B acylhydrazine thiourea (RhBHA), reversible "on-off" ring reaction of RhBHA at various pH values, and thermosensitive property of poly(N-isopropyl acrylamide) (PNIPAM), a novel linear polymer P(NIPAM-co-RhBHA)-NP was prepared via a series of chemical reactions. Firstly, 4-(2-aminoethyl)amino-N-aminopropane-1, 8-naphthalimide (NP-NH₂) and RhBHA were prepared respectively, and they were used as the donor and acceptor to construct a fluorescence resonance energy transfer (FRET) system. Secondly, incorporating RhBHA into PNIPAM by reversible addition-fragmentation chain transfer polymerization (RAFT), P(NIPAM-co-RhBHA) was synthesized. Finally, P(NIPAM-co-RhBHA)-NP was fabricated by amide condensation between NP-NH₂ and the as-prepared P(NIPAM-co-RhBHA). The structure of P(NIPAM-co-RhBHA)-NP was characterized via ¹H NMR, FTIR, UV-vis and GPC. The fluorescence responsive behavior of the polymer to environmental temperature and pH value was investigated by photoluminescence (PL) in buffer solutions, and the mechanism was discussed in detail. The results indicate that, in an acidic solution, energy can be transferred from NP-NH₂ moieties to RhBHA moieties via FRET mechanism, either pH values or environmental temperatures play important roles to affect the fluorescence emission of P(NIPAM-co-RhBHA)-NP.
1. [1]
  Dai, S.; Ravi, P.; Tam, K. C. Soft Matter 2009, 5, 2513.
2. [2]
  Song, Q. S.; Yang, Y.; Gao, K.; Ma, H. H. J. Lumin. 2013, 136, 437. doi: 10.1016/j.jlumin.2012.12.005
3. [3]
  Dai, S.; Ravi, P.; Tam, K. C. Soft Matter 2008, 4, 435. doi: 10.1039/b714741d
4. [4]
  Yang, Y.; Song, Q. S.; Gao, K.; Ma, H. H.; Yang, S. S.; Li, T. J. Appl. Polym. Sci. 2014, 131, 1001.
5. [5]
  Li, C. H.; Hu, J. M.; Liu, S. Y. Soft Matter 2012, 8, 7096. doi: 10.1039/c2sm25582k
6. [6]
  Kim, H. J.; Lee, M. H.; Mutihac, L. Chem. Soc. Rev. 2012, 41, 1173. doi: 10.1039/C1CS15169J
7. [7]
  Song, Q. S.; Yang, S. S.; Sheng, R.; Li, T. Acta Chim. Sinica 2014, 72, 89. doi: 10.6023/A13101064
8. [8]
  Förster, T. Ann. Phys. 1984, 2, 55.
9. [9]
  Chen, K. J.; Chiu, Y. L.; Chen, Y. M.; Ho, Y. C.; Sung, H. W. Biomaterials 2011, 32, 2586. doi: 10.1016/j.biomaterials.2010.11.069
10. [10]
  Kim, G. B.; Kim, Y. P. Theranostics 2012, 2, 127. doi: 10.7150/thno.3476
11. [11]
  Uchiyama, S.; Kimura, K.; Gota, C.; Okabe, K.; Kawamoto, K.; Inada, N.; Yoshihara, T.; Tobita, S. Chem. Eur. J. 2012, 18, 9552. doi: 10.1002/chem.201200597
12. [12]
  Liu, S. Y.; Hu, J. M.; Li, C. H. Langmuir 2011, 44, 4699.
13. [13]
  Song, Q. S.; Gao, K.; Yao, W.; Yang, Y.; Ma, H. H. Acta Chim. Sinica 2012, 70, 2155. doi: 10.6023/A12070417
14. [14]
  Kim, H. N.; Lee, M. H.; Kim, H. J. Chem. Soc. Rev. 2008, 37, 1465. doi: 10.1039/b802497a
15. [15]
  Yang, Y. K.; Yook, K. J.; Tea, J. J. Am. Chem. Soc. 2005, 127, 16760. doi: 10.1021/ja054855t
16. [16]
  Yu, M. X.; Shi, M.; Chen, Z. G. Chem. Eur. J. 2008, 14, 6892. doi: 10.1002/chem.v14:23
17. [17]
  Shiraishi, Y.; Miyamoto, R.; Zhang, X. Org. Lett. 2007, 9, 3921. doi: 10.1021/ol701542m
18. [18]
  Hu, J. M.; Li, C. H.; Liu, S. Y. Langmuir 2010, 26, 724. doi: 10.1021/la9024102
19. [19]
  Ko, S. K.; Yang, Y. K.; Tae, J.; Shin, I. J. Am. Chem. Soc. 2006, 128, 14150. doi: 10.1021/ja065114a
20. [20]
  Chang, W. B.; Li, K. A. Concise Handbook of Analytical Chemistry, Peking University Press, Beijing, 1981, pp. 262～263.
21. [21]
  Li, T.; Zhou, W.; Song, Q. S.; Fang, W. C. J. Photochem. Photobiol. A 2015, 302, 51. doi: 10.1016/j.jphotochem.2015.01.012
22. [22]
  Li, C. H.; Liu, S. Y. J. Mater. Chem. 2010, 20, 10716. doi: 10.1039/c0jm01828g
23. [23]
  Birks, J. B. Photophysics of Aromatic Molecules, Wiley, New York, 1970, pp. 73～75.
24. [24]
  Ding, D.; Li, K.; Liu, B.; Tang, B. Z. Acc. Chem. Res. 2013, 46, 2441. doi: 10.1021/ar3003464
25. [25]
  Xu, J. G.; Wang, Z. B. Fluorescence Analysis, Science Press, Beijing, 2006, pp. 12～13.
26. [26]
  Zakerhamidi, M. S.; Ghanadzadeh, A.; Moghadam, M. Spectrochim. Acta Part A 2011, 78, 961. doi: 10.1016/j.saa.2010.12.002
27. [27]
  Osada, Y.; Gong, J. P. Adv. Mater. 1998, 10, 827. doi: 10.1002/(ISSN)1521-4095
28. [28]
  Galave, I.; Mattiasson, B. Enzyme. Microb. Tech. 1993, 15, 354. doi: 10.1016/0141-0229(93)90122-I
29. [29]
  Vogt, A. P.; Gondi, S. R.; Sumerlin, B. S. Aust. J. Chem. 2007, 60, 396. doi: 10.1071/CH07077
30. [30]
  Zeng, H. B.; Li, Y. B.; Zhang, H. Y.; Wang, X. G. Acta Polym. Sinica 2004, (3), 327.
31. [31]
  Lai, J. T.; Filla, D.; Shea, R. Macromolecules 2002, 35, 6754. doi: 10.1021/ma020362m
32. [32]
  Vonlanthen, M.; Finney, N. S. J. Org. Chem. 2013, 78, 3980. doi: 10.1021/jo4003129
33. [33]
  Yang, X.; Guo, X.; Zhao, Y. Talanta 2002, 57, 883.
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Dual Stimulus-responsive Fluorescence Behavior and Mechanism of P(NIPAM-co-RhBHA)-NP

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

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通讯作者: 陈斌, bchen63@163.com