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]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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-. doi: 10.3866/PKU.WHXB202309045
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  Zeyi Yan , Ruitao Liu , Xinyu Qi , Yuxiang Zhang , Lulu Sun , Xiangyuan Li , Anchao Feng . Exploration of Suspension Polymerization: Preparation and Fluorescence Stability of Perovskite Polystyrene Microbeads. University Chemistry, 2025, 40(4): 72-79. doi: 10.12461/PKU.DXHX202405110
10. [10]
  Yuan CONG , Yunhao WANG , Wanping LI , Zhicheng ZHANG , Shuo LIU , Huiyuan GUO , Hongyu YUAN , Zhiping ZHOU . Construction and photocatalytic properties toward rhodamine B of CdS/Fe₃O₄ heterojunction. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2241-2249. doi: 10.11862/CJIC.20240219
11. [11]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
12. [12]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
13. [13]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
14. [14]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
15. [15]
  Feng Lu , Tao Wang , Qi Wang . Preparation and Characterization of Water-Soluble Silver Nanoclusters: A New Design and Teaching Practice in Materials Chemistry Experiment. University Chemistry, 2025, 40(4): 375-381. doi: 10.12461/PKU.DXHX202406005
16. [16]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
17. [17]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
18. [18]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
19. [19]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
20. [20]
  Zhifeng CAI , Ying WU , Yanan LI , Guiyu MENG , Tianyu MIAO , Yihao ZHANG . Effective detection of malachite green by folic acid stabilized silver nanoclusters. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 983-993. doi: 10.11862/CJIC.20240394

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(3028)
HTML views(1209)

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