Citation: Liu Ya-lan, Wang Zheng-ke, Qin Wei, Hu Qiao-ling, Tang Ben Zhong. Fluorescent Detection of Cu(Ⅱ) by Chitosan-based AIE Bioconjugate[J]. Chinese Journal of Polymer Science, ;2017, 35(3): 365-371. doi: 10.1007/s10118-017-1876-y shu

Fluorescent Detection of Cu(Ⅱ) by Chitosan-based AIE Bioconjugate

Liu Ya-lan ^a,b ,
Wang Zheng-ke ^a,b,, ,
Qin Wei ^c ,
Hu Qiao-ling ^a,b,, ,
Tang Ben Zhong ^c,,

a.
Ministry of Education Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China
b.
Key Laboratory of Adsorption and Separation Materials & Technologies of Zhejiang Province, Hangzhou 310027, China
c.
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong, China

Corresponding author: Wang Zheng-ke, wangzk@zju.edu.cn Hu Qiao-ling, huql@zju.edu.cn Tang Ben Zhong, tangbenz@ust.hk
Received Date: 30 July 2016
Revised Date: 17 September 2016
Accepted Date: 30 September 2016

Fund Project: the National Natural Science Foundation of China 21104067, 21274127, 21374099 and 51473144the Key Science Technology Innovation Team of Zhejiang Province 2013TD02

Detection of Cu(Ⅱ) is very important in disease diagnose, biological system detection and environmental monitoring. Previously, we found that the product TPE-CS prepared by attaching the chromophores of tetraphenylethylene (TPE) to the chitosan (CS) chains showed excellent fluorescent properties. In this study, we tried to use TPE-CS for detecting Cu(Ⅱ) because of the stable complexation of CS with heavy metals and the luminosity mechanism of the Restriction of Intramolecular Rotations (RIR) for aggregation-induced emission (AIE)-active materials. The fluorescence intensity changed when TPE-CS was contacted with different metal ions, to be specific, no change for Na⁺, slightly increase for Hg²⁺, Pb²⁺, Zn²⁺, Cd²⁺, Fe²⁺, Fe³⁺ due to the RIR caused by the complexation between CS and metal ions. However, for Cu²⁺, an obvious fluorescence decrease was observed because of the Photoinduced-Electron-Transfer (PET). Moreover, we found that the quenched FL intensity of TPE-CS was proportional to the concentration of Cu(Ⅱ) in the range of 5 μmol/L to 100 μmol/L, which provided a new way to quantitatively detect Cu(Ⅱ). Besides, TPE-CS has excellent water-solubility as well as absorbability (the percentage of removal, R=84%), which is an excellent detection probe and remover for Cu(Ⅱ).
- Aggregation-induced emission,
- Chitosan,
- Cu(Ⅱ),
- Fluorescent detection
1. [1]
  Wang, F.Y., Li, Y.X., Li, W.Y., Chen, J., Zhang, Q.F., Shahzad, S.A. and Yu, C., Talanta, 2015, 132: 72
2. [2]
  2 Georgopoulos, P.G., Roy, A., Yonone, L.M.J., Opiekun, R.E. and Lioy, P.J.J., Toxicol. Environ. Health B: Crit. Rev., 2001, 4(4): 341
3. [3]
  Bonham, M., O'Connor, J.M., Hannigan, B.M. and Strain, J.J., Brit. J. Nutr., 2007, 87(5): 393
4. [4]
  4 Sanji, T., Nakamura, M. and Tanaka, M., Tetrahedron Lett., 2011, 52(26): 3283
5. [5]
  Zietz, B.P., de Vergara, J.D. and Dunkelberg, H., Environ. Res., 2003, 92(2): 129
6. [6]
  6 Kumbhar, H.S., Yadav, U.N., Gadilohar, B.L. and Shankarling, G.S., Sensor Actuat. B: Chem., 2014, 203: 174
7. [7]
  Kandasamy, K., Ganesabaskaran, S., Pachamuthu, M.P. and Ramanathan, A., Spectrochim. Acta A, 2015, 148: 184 doi: 10.1016/j.saa.2015.04.005
8. [8]
  8 Gonzales, A.P., Firmino, M.A., Nomura, C.S., Rocha, F.R., Oliveira, P.V. and Gaubeur, I., Anal. Chim. Acta, 2009, 636(2): 198
9. [9]
  Becker, J.S., Zoriy, M.V., Pickhardt, C., Palomero, G.N. and Zilles, K., Anal. Chem., 2005, 77(10): 3208
10. [10]
  10 Chen, X.L., Zeng, W.F., Yang, X.D., Lu, X.W., Qu, J.Q. and Liu, R.Y., Chinese J. Polym. Sci., 2016, 34(3): 324
11. [11]
  Cotruvo, J.A., Jr., Aron, A.T., Ramos, T.K.M. and Chang, C.J., Chem. Soc. Rev., 2015, 44(13): 4400
12. [12]
  12 Domaille, D.W., Que, E.L. and Chang, C.J., Nat. Chem. Biol., 2008, 4(3): 168
13. [13]
  Yuan, W.Z., Lu, P., Chen, S.M., Lam, J.W.Y., Wang, Z.M., Liu, Y., Kwok, H.S., Ma, Y.G. and Tang, B.Z., Adv. Mater., 2010, 22(19): 2159
14. [14]
  14 Hong, Y.N., Chen, S.J., Leung, C.W.T., Lam, J.W.Y., Liu, J.Z., Tseng, N.W., Kwok, R.T.K., Yu, Y., Wang, Z.K. and Tang, B.Z., ACS Appl. Mater. Inter., 2011, 3(9): 3411
15. [15]
  Feng, H.T., Song, S., Chen, Y.C., Shen, C.H. and Zheng, Y.S., J. Mater. Chem. C, 2014, 2(13): 2353
16. [16]
  16 Nie, J.Y., Wang, Z.K., Zhang, K. and Hu, Q.L., RSC Adv., 2015, 5(47): 37346
17. [17]
  Nie, J.Y., Wang, Z.K., Zhang, J.Z., Yang, L., Pang, Y.C. and Hu, Q.L., RSC Adv., 2015, 5(83): 68243
18. [18]
  18 Huang, X.F., Jia, J.W., Wang, Z.K. and Hu, Q.L., Chinese J. Polym. Sci., 2014, 33(2): 284
19. [19]
  Zhang, K., Zhuang, P.Y., Wang, Z.K., Li, Y.L., Jiang, Z.Q., Hu, Q.L., Liu, M.Y. and Zhao, Q.X., Carbohydr. Polym., 2012, 90(4): 1515
20. [20]
  20 Nie, J.Y., Lu, W.T., Ma, J.J., Yang, L., Wang, Z.K., Qin, A. and Hu, Q.L., Sci. Rep., 2015, 5: 7635
21. [21]
  Fang, J.D., Zhang, K., Jia, J.W., Wang, Z.K. and Hu, Q.L., RSC Adv., 2015, 5(120): 99418
22. [22]
  22 Wang, Z.K. and Hu, Q.L., Biomed. Mater., 2010, 5(4): 045007
23. [23]
  Wang, Z.K., Hu, Q.L. and Wang, Y.X., Sci. China Chem., 2011, 54(2): 380
24. [24]
  24 Huang, X.F., Sun, Y.F., Nie, J.Y., Lu, W.T., Yang, L., Zhang, Z.L., Yin, H.P., Wang, Z.K. and Hu, Q.L., Int. J. Biol. Macromol., 2015, 75: 322
25. [25]
  Ke, J.H., Wang, Z.K., Li, Y.Z. and Hu, Q.L., Chinese J. Polym. Sci., 2012, 30(3): 436 doi: 10.1007/s10118-012-1133-3
26. [26]
  26 Wang, Z.K., Hu, Q.L. and Cai, L., Chinese J. Polym. Sci., 2010, 28(5): 801
27. [27]
  Zhang, K., Zhao, M., Cai, L., Wang, Z.K., Sun, Y.F. and Hu, Q.L., Chinese J. Polym. Sci., 2010, 28(4): 555 doi: 10.1007/s10118-010-9087-9
28. [28]
  28 Lee, S.J., Lee, S.S., Lah, M.S., Hong, J.M. and Jung, J.H., Chem. Commun., 2006, (43): 4539
29. [29]
  Wang, Z.K., Chen, S.J., Lam, J.W.Y., Qin, W., Kwok, R.T., Xie, N., Hu, Q. and Tang, B.Z., J. Am. Chem. Soc., 2013, 135(22): 8238
30. [30]
  30 Jia, J.W., Wang, Z.K., Lu, W.T., Yang, L., Wu, Q.W., Qin, W., Hu, Q.L. and Tang, B.Z., J. Mater. Chem. B, 2014, 2: 8406
31. [31]
  Wang, Z.K., Liu, Y.L., Jia, J.W., Chen, S.J., Qin, W., Hu, Q.L. and Tang, B.Z., J. Mater. Chem. B, 2016, 4: 5265
32. [32]
  32 Wang, Z.K., Nie, J.Y., Qin, W., Hu, Q.L. and Tang, B.Z., Nat. Commun., 2016, 7: 12033
33. [33]
  Li, M., Hong, Y.N., Wang, Z.K., Chen, S.J., Gao, M., Kwok, R.T.K., Qin, W., Lam, J.W.Y., Zheng, Q.C. and Tang, B.Z., Macromol. Rapid Commun., 2013, 34: 767
34. [34]
  34 Hong, Y.N., Lam, J.W.Y. and Tang, B.Z., Chem. Commun., 2009(29): 4332
35. [35]
  Huang, H., Shi, F.P., Li, Y.N., Niu, L., Gao, Y., Shah, S.M. and Su, X.G., Sensor Actuat. B: Chem., 2013, 178: 532 doi: 10.1016/j.snb.2013.01.003
36. [36]
  36 Xu, G.Y., Wang, J.F., Si, G.F., Wang, M.H., Xue, X., Wu, B.X. and Zhou, S.S., Sensor Actuat. B: Chem., 2016, 230: 684
37. [37]
  Li, Z.A., Lou, X.D., Yu, H.B., Li, Z. and Qin, J.G., Macromolecules, 2008, 41(20): 7433 doi: 10.1021/ma8013096
38. [38]
  38 Zhang, S.R., Wang, Q., Tian, G.H. and Ge, H.G., Mater. Lett., 2014, 115: 233
39. [39]
  Wang, X., Chen, Q.Y., Yin, Z.L., Hu, H.P. and Xiao, Z.L., J. Cent. South. Univ. Technol., 2011, 18: 48 doi: 10.1007/s11771-011-0657-y
40. [40]
  40 Wu, Z.C., Wang, Z.Z., Liu, J., Yin, J.H. and Kuang, S.P., Colloid. Surface. A, 2016, 499: 141
41. [41]
  Azzam, E.M., Eshaq, G., Rabie, A.M., Bakr, A.A., Abd, E., A.A., El Metwally, A.E. and Tawfik, S.M., Int. J. Biol. Macromol., 2016, 89: 507 doi: 10.1016/j.ijbiomac.2016.05.004
42. [42]
  42 Cao, W.X., Lin, G.L., Jin, L.S. and Wei, Z.H., Liaoning Chemical Industry (in Chinese), 2007, 36(8): 529
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