Citation: Liu Ruijiao, Zeng Jing. Study on a Novel Colorimetric and Off-On Fluorescent Chemosensor with Aggregation-Induced Emission Effect for Detection of Fe³⁺ in Aqueous Solution[J]. Chinese Journal of Organic Chemistry, ;2017, 37(12): 3274-3281. doi: 10.6023/cjoc201706037 shu

Study on a Novel Colorimetric and Off-On Fluorescent Chemosensor with Aggregation-Induced Emission Effect for Detection of Fe³⁺ in Aqueous Solution

Liu Ruijiao ^a ,
Zeng Jing ^a,,

College of Chemistry and Chemical Engineering, Xinjiang Normal University, Urumqi 830054

Corresponding author: Zeng Jing, zengjing800111@163.com; lrjxjnu@163.com
Received Date: 28 June 2017
Revised Date: 8 August 2017
Available Online: 15 December 2017
Fund Project: the Doctoral Scientific Research Foundation of Xinjiang Normal University XJNUBS1508Project supported by the Natural Science Foundation of Xinjiang Uygur Aotonomous Region (No. 2015211B024) and the Doctoral Scientific Research Foundation of Xinjiang Normal University (No. XJNUBS1508)the Natural Science Foundation of Xinjiang Uygur Aotonomous Region 2015211B024

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A novel tetraphenylethyene-functionalized rhodamine derivative (TPE-RhB) was designed and synthesized. FT-IR, NMR, MS, elemental analysis, cyclic voltammetry electrochemical analysis, UV-Vis, and molecular fluorescence were used to study its structure, electrochemical and optical properties. These results showed that the electron affinity of TPE-RhB was 3.66 eV, which is expected to develop electron-transporting material. A significant aggregation-induced emission (AIE) effect of TPE-RhB was found through solution fluorescence test in different V(EtOH):V(H₂O) mixed solvents. Furthermore, sensor TPE-RhB displayed highly seletive and sensitive off-on fluorescence response and naked-eye color change to Fe³⁺ in EtOH/H₂O (V:V=1:1, Tris-HCl pH 7.0) solution. The association constant between TPE-RhB and Fe³⁺ was detected to be 3.12×10³ and the detection limit was calculated to be 3.53×10^-7 mol·L^-1. The probe TPE-RhB also showed a good linearity (R²=0.9915) in the range of 60~180 μmol/L of Fe³⁺ ion. The mechanisms had been supported by Job's plot evalution, fluorescence titrations, and ¹H NMR spectroscopic studies.
- tetraphenylethyene,
- rhodamine B,
- aggregation-induced emission (AIE) effect,
- fluorescent chemosensor,
- optoelectronic material
1. [1]
  Luo, J.-D.; Xie, Z.-L.; Lam, J. W. Y.; Lin, C. Chem. Commun. 2001, 18, 1740.
2. [2]
  You, X.; Zhang, G.-X.; Zhan, C.; Wang, Y.-C.; Zhang, D.-Q. ACS Symp. Ser. 2016, 93, 1227.
3. [3]
  Wang, Q.; Li, Z.; Tao, D.-D.; Zhang, Q.; Zhang, P.; Guo, D.-P.; Jiang, Y.-B. Chem. Commun. 2016, 52, 12929. doi: 10.1039/C6CC06075G
4. [4]
  Zhang, G.-X.; Hu, F.; Zhang, D.-Q. Langmuir 2015, 31, 4593. doi: 10.1021/la5029367
5. [5]
  Wang, L.-Y.; Yang, L.-L.; Cao, D.-R. Curr. Org. Chem. 2014, 18, 1028. doi: 10.2174/1385272819666140407214006
6. [6]
  Yang, Y.; Huang, Y.-Y.; Zhang, G.-X.; Zhao, R.; Zhang, D.-Q. Acta Chim. Sinica 2016, 74, 871(in Chinese). doi: 10.11862/CJIC.2016.115
7. [7]
  Li, Z.-Z.; Huo, Y.-P.; Yang, X.-H.; Ji, S.-M. Chin. J. Org. Chem. 2016, 36, 2317(in Chinese).
8. [8]
  Gabr, M. T.; Pigge, F. C. Dalton Trans. 2016, 45, 14039. doi: 10.1039/C6DT02657E
9. [9]
  Jiang, G.-Y.; Liu, X.; Wu, Y.-Q.; Wang, J.-G.; Dong, X.-B.; Zhang, G.-X.; Li, Y.-D.; Fan, X.-L. RSC Adv. 2016, 6, 59400. doi: 10.1039/C6RA10878D
10. [10]
  Xiong, J.-B.; Xie, W.-Z.; Sun, J.-P.; Wang, J.-H.; Zhu, Z.-H.; Feng, H.-T.; Guo, D.; Zhang, H.; Zheng, Y.-S. J. Org. Chem. 2016, 81, 3720. doi: 10.1021/acs.joc.6b00371
11. [11]
  Zhao, N.; Chen, S.-J.; Hong, Y.-N.; Tang, B.-Z. Chem. Commun. 2015, 51, 13599. doi: 10.1039/C5CC04731E
12. [12]
  Huang, J.; Li, Q.-Q.; Li, Z.-J. J. Mol. Eng. Mater. 2013, 1, 1.
13. [13]
  Wu, F.; Shan, Y.-H.; Li, X.-L.; Song, Q.-L.; Zhu, L.-N. Org. Electron. 2016, 39, 323. doi: 10.1016/j.orgel.2016.10.022
14. [14]
  Wu, F.; Liu, J.-L.; Wang, G.; Song, Q.-L.; Zhu, L.-N. Chem. Eur. J. 2016, 22, 16636. doi: 10.1002/chem.201603672
15. [15]
  Zhao, D.-Y. ACS Symp. Ser. 2016, 2, 151.
16. [16]
  Takeda, T.; Yamamoto, S.; Mitsuishi, M.; Akutagawa, T. Org. Biomol. Chem. 2016, 14, 8922. doi: 10.1039/C6OB01110A
17. [17]
  Ramya, A. N.; Joseph, M. M.; Nair, J. B.; Karunakaran, V.; Narayanan, N.; Maiti, K. K. ACS Appl. Mater. Inter. 2016, 8, 10220. doi: 10.1021/acsami.6b01908
18. [18]
  Huang, J.; Yang, M.; Yang, J.; Tang, R.; Ye, S.; Li, Q.; Li, Z. Org. Chem. Front. 2015, 12, 1608.
19. [19]
  Lu, D.-Q.; He, L.; Wang, Y.-Y.; Xiong, M.-Y.; Hu, M.-M.; Liang, H.; Huan, S.-Y.; Zhang, X.-B.; Tan, W.-H. Talanta 2017, 167, 550. doi: 10.1016/j.talanta.2017.02.064
20. [20]
  Akul, S. G.; Kamaldeep, P.; Vijay, L. Sens. Actuators, B 2017, 246, 653. doi: 10.1016/j.snb.2017.02.080
21. [21]
  Yan, Y.-Y.; Che, Z.-P.; Yu, X.; Zhi, X.-Y.; Wang, J.-J.; Xu, H. Bioorg. Med. Chem. 2013, 21, 508. doi: 10.1016/j.bmc.2012.11.005
22. [22]
  Chen, X.; Pradhan, T.; Wang, F.; Kim, J. S.; Yoon, J. Chem. Rev. 2012, 112, 1910. doi: 10.1021/cr200201z
23. [23]
  Sun, W.; Hu, D.-Y.; Wu, Z.-B.; Song, B.-A.; Yang, S. Chin. J. Org. Chem. 2011, 31, 997(in Chinese).
24. [24]
  Liu, H.-Y.; Wan, X.-J.; Liu, T.-Q.; Li, Y.-Q.; Yao, Y.-W. Sens. Actuators, B 2014, 200, 191. doi: 10.1016/j.snb.2014.04.027
25. [25]
  Yan, L.-R.; Yang, M.-P.; Leng, X.; Zhang, M.; Long, Y.; Yang, B.-Q. Tetrahedron 2016, 72, 4361 doi: 10.1016/j.tet.2016.05.082
26. [26]
  Fan, S.-M.; Yang, W.-G.; Hao, J.-F.; Li, H.-G.; Zhao, W.-D.; Zhang, J.; Hu, Y.-H. J. Photochem. Photobiol., A 2016, 328, 129. doi: 10.1016/j.jphotochem.2016.05.017
27. [27]
  Li, S.; Zhang, D.; Xie, X.-Y.; Ma, S.-G.; Xu, Z.-H.; Gao, Y.-F.; Ye, Y. Sens. Actuators, B 2016, 224, 661. doi: 10.1016/j.snb.2015.10.086
28. [28]
  Liu, X.-J.; Zhang, M.; Yang, M.-P.; Li, B.; Zhao, C.; Yang, B.-Q. Tetrahedron 2015, 71, 8194. doi: 10.1016/j.tet.2015.08.031
29. [29]
  Xiao, H.-F.; Zhang, M.; Liu, J.; Han, Z.-X.; Yang, L.-Q.; Wu, X.-Y. Chin. J. Org. Chem. 2016, 36, 2413(in Chinese).
30. [30]
  Hou, S.-H.; Qu, Z.-G.; Zhong, K.-L.; Bian, Y.-J.; Tang, L.-J. Chin. J. Org. Chem. 2016, 36, 768(in Chinese).
31. [31]
  Meng, W.-F.; Yang, M.-P.; Cheng, Z.; Li, S.-N.; Yang, B.-Q. Chin. J. Org. Chem. 2014, 34, 398(in Chinese).
32. [32]
  Wu, F.; Tian, W.-J.; Shen, J.-E. Chin. J. Lumin. 1998, 19, 158(in Chinese).
33. [33]
  Dong, Y. Q.; Lam, J. W. Y.; Qin, A. J.; Sun, J. X.; Liu, J. Z.; Li, Z.; Sun, J. Z.; Sung, H. H. Y.; Williams, I. D.; Kwokc, H. S.; Tang, B. Z. Chem. Commun. 2007, 3255.
34. [34]
  Liu, R.-J.; Zeng, J.; Wang, H. Chin. J. Lumin. 2017, 38, 862(in Chinese).
35. [35]
  Zhou, Z.-G.; Yu, M.-X.; Li, F.-Y. Chem. Commun. 2008, 29, 3387.
36. [36]
  Han, X.; Wang, D.-E.; Chen, S.; Zhang, L.-L.; Guo, Y.-D.; Wang, J.-Y. Anal. Methods 2015, 7, 4231. doi: 10.1039/C5AY00568J
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Study on a Novel Colorimetric and Off-On Fluorescent Chemosensor with Aggregation-Induced Emission Effect for Detection of Fe3+ in Aqueous Solution

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通讯作者: 陈斌, bchen63@163.com

Study on a Novel Colorimetric and Off-On Fluorescent Chemosensor with Aggregation-Induced Emission Effect for Detection of Fe³⁺ in Aqueous Solution