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

Figures(11)

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
1. [1]
  Yubin Su , Chenyu Yao , Shuyan Chen , Lisha Xu , Min Peng , Yawen Wang , Yu Peng , Jianfeng Zheng . 一种聚集诱导发光荧光探针的合成及其在指纹显影中的应用——本科生综合性化学实验探索. University Chemistry, 2026, 41(5): 70-78. doi: 10.12461/PKU.DXHX202511031
2. [2]
  Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064
3. [3]
  Yuting DU , Jing YUAN , Peiyao DENG . Synthesis and application of a fluorescent probe for the detection of reduced glutathione. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1331-1337. doi: 10.11862/CJIC.20240461
4. [4]
  Yunshang YANG , Weiliang ZHAO , Zetai HU , Yingpeng ZHANG . Synthesis and application of a carbazole-pyrazole-based ratiometric fluorescent probe for detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2026, 42(10): 2153-2161. doi: 10.11862/CJIC.20260082
5. [5]
  Qiang HU , Zhiqi CHEN , Zhong CHEN , Xu WANG , Weina WU . Pyridinium-chalcone-based ClO^- fluorescent probe: Preparation and biological imaging applications. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1789-1795. doi: 10.11862/CJIC.20250086
6. [6]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
7. [7]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
8. [8]
  Liangling Tan , Chonghua Zhang , Xianjun Liu , Yiting Xu , Wanqiang Liu . 科教融合导向的化学综合实验设计——以铜离子特异性荧光探针的研发与应用为例. University Chemistry, 2026, 41(10): 316-325. doi: 10.12461/PKU.DXHX202510041
9. [9]
  Xia ZHANG , Yushi BAI , Xi CHANG , Han ZHANG , Haoyu ZHANG , Liman PENG , Shushu HUANG . Preparation and photocatalytic degradation performance of rhodamine B of BiOCl/polyaniline. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 913-922. doi: 10.11862/CJIC.20240255
10. [10]
  Pengli GUAN , Renhu BAI , Xiuling SUN , Bin LIU . Trianiline-derived aggregation-induced emission luminogen probe for lipase detection and cell imaging. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1817-1826. doi: 10.11862/CJIC.20250058
11. [11]
  Xinrong Wu , Yingying Ren , Jianxue Wang , Lijin Yang , Jia Jia , Nan Li , Na Zhao . 聚光捕胺——高灵敏胺响应型聚集诱导发光探针的合成及传感应用. University Chemistry, 2026, 41(5): 180-189. doi: 10.12461/PKU.DXHX202509129
12. [12]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
13. [13]
  Shunping WANG , Chuandong GE , Shuguang QU , Tianduo LI , Shaomin WANG , Qingyuan YANG . Synthesis of a fluorescent probe based on urea-based coordination and Si—O bond cleavage for F^- and Cr(Ⅵ) detection. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 297-308. doi: 10.11862/CJIC.20250214
14. [14]
  Yao Ma , Xin Zhao , Hongxu Chen , Wei Wei , Liang Shen . Progress and Perspective of Perovskite Thin Single Crystal Photodetectors. Acta Physico-Chimica Sinica, 2025, 41(4): 100030-0. doi: 10.3866/PKU.WHXB202309045
15. [15]
  Wei LI , Jianjie XU , Linlin WANG , Chuanbing HOU , Hongliang HAN , Qionghua JIN . Synthesis, structure, and photocatalytic properties of {PMo₁₂}-based rare-earth tetraisopropyl ethylenediphosphonate complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(10): 2077-2091. doi: 10.11862/CJIC.20260220
16. [16]
  Xinxin YU , Yongxing LIU , Xiaohong YI , Miao CHANG , Fei WANG , Peng WANG , Chongchen WANG . Photocatalytic peroxydisulfate activation for degrading organic pollutants over the zero-valent iron recovered from subway tunnels. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 864-876. doi: 10.11862/CJIC.20240438
17. [17]
  Yuanqing Wang , Yusong Pan , Hongwu Zhu , Yanlei Xiang , Rong Han , Run Huang , Chao Du , Chengling Pan . Enhanced Catalytic Activity of Bi₂WO₆ for Organic Pollutants Degradation under the Synergism between Advanced Oxidative Processes and Visible Light Irradiation. Acta Physico-Chimica Sinica, 2024, 40(4): 2304050-0. doi: 10.3866/PKU.WHXB202304050
18. [18]
  Mi Wen , Baoshuo Jia , Yongqi Chai , Tong Wang , Jianbo Liu , Hailong Wu . Improvement of Fluorescence Quantitative Analysis Experiment: Simultaneous Determination of Rhodamine 6G and Rhodamine 123 in Food Using Chemometrics-Assisted Three-Dimensional Fluorescence Method. University Chemistry, 2025, 40(4): 390-398. doi: 10.12461/PKU.DXHX202405147
19. [19]
  Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
20. [20]
  Xiaohong Li , Huanjiang Wang , Fang Tan , Xiaohua Cai , Yingchun Luo , Yanli Leng , Guoyong Zhou , Zhu Wen . Research on the Project-Driven Teaching Model in the Context of New Engineering: A Case Study of the Development of a “Portable Metal ions and Pesticide Residues Intelligent Detection System”. University Chemistry, 2026, 41(1): 204-212. doi: 10.12461/PKU.DXHX202510037

Get Citation

PDF

XML

Metrics

PDF Downloads(18)
Abstract views(5181)
HTML views(1705)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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

Metrics

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