Citation: Zhang Youming, Han Bingbing, Lin Qi, Mao Pengpeng, Chen Jinfa, Yao Hong, Wei Taibao. Synthesis and Fe³⁺ Sensing Properties of the Chemosensor Based on Functionalized Naphthalimide Schiff Base Derivative[J]. Chinese Journal of Organic Chemistry, ;2018, 38(7): 1800-1805. doi: 10.6023/cjoc201711002 shu

Synthesis and Fe³⁺ Sensing Properties of the Chemosensor Based on Functionalized Naphthalimide Schiff Base Derivative

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Corresponding author: Zhang Youming, Wei Taibao, weitaibao@126.com
Received Date: 1 November 2017
Revised Date: 17 January 2018
Available Online: 16 July 2018
Fund Project: the National Natural Science Foundation of China 21262032the National Natural Science Foundation of China 21661028the National Natural Science Foundation of China 21662031the National Natural Science Foundation of China 21574104Project supported by the National Natural Science Foundation of China (Nos. 21662031, 21661028, 21574104, 21262032)

Figures(7)

A novel sensor molecule 2-hydroxyl-1-naldehyde-N-(4-aminophenyl)-1, 8-naphthalimide (H1) based on functionalized naphthalimide Schiff Base derivative was synthesized. H1 was characterized by ¹H NMR, ¹³C NMR and HRMS. Furthermore, its fluorescence properties were studied in dimethyl sulfoxide (DMSO)/H₂O (V:V=7:3) solutions. Its maximum emission wavelength was 496 nm. The solution of H1 has yellow-green fluorescence under the UV lamp (365 nm). H1 showed fluorescence-colorimetric dual channel identification ability for Fe³⁺. With the addition of various metal ions into the H1 solution, only Fe³⁺ caused the fluorescence of the H1 quenching and the color disappeared. Other cations such as Ag⁺, Ca²⁺, Ba²⁺, Co²⁺, Ni²⁺, Cd²⁺, Pb²⁺, Zn²⁺, Cu²⁺, Mg²⁺ and Hg²⁺ could not induce similar response. The results of anti-disturbance experiment demonstrated that other cations can not interfere in the detection of Fe³⁺. H1 has good sensitivity for Fe³⁺, the fluorescence and UV-Vis detection limits of the H1 for Fe³⁺ are 3.04×10^-8 and 2.71×10^-6 mol·L^-1, respectively. Finally, the test strips based on the H1 were prepared, which could conveniently and efficiently detect Fe³⁺ in water.
- naphthalimide derivative,
- Schiff base,
- sensor molecule,
- fluorescence-colorimetric dual channel identification,
- Fe³⁺
1. [1]
  Lin, Q.; Chen, P.; Liu, J.; Fu, Y.-P.; Zhang, Y.-M.; Wei, T.-B. Prog. Chem. 2013, 25, 1177 (in Chinese).
2. [2]
  Lin, Q.; Liu, X.; Chen, P.; Wei, T.-B.; Zhang, Y.-M. Prog. Chem. 2013, 25, 2131 (in Chinese).
3. [3]
  Zhang, P.; Zhang, Y.-M.; Lin, Q.; Yao, H.; Wei, T.-B. Chin. J. Org. Chem. 2014, 34, 1300 (in Chinese).
4. [4]
  Li, C.-W.; Yang, D.; Yin, B.; Guo, Y. Chin. J. Org. Chem. 2016, 36, 787 (in Chinese).
5. [5]
  Graham, R. C.; Hamilton, S. K.; Sahoo, S. K.; Narinder Singh, N. K.; Barry, W. H.; John, F. C. Chem. Soc. Rev. 2015, 44, 4415. doi: 10.1039/C4CS00365A
6. [6]
  Guo, X.-F.; Qian, X.-H.; Jia, L.-H. J. Am. Chem. Soc. 2004, 126, 2272. doi: 10.1021/ja037604y
7. [7]
  Koner, A. L.; Schatz, J.; Nau, W. M.; Pischel, U. J. Org. Chem. 2007, 72, 3889. doi: 10.1021/jo070268+
8. [8]
  Huang, X.-M.; Guo, Z.-Q.; Zhu, W.-H.; Xie, Y. S.; Tian, H. Chem. Commun. 2008, 5143.
9. [9]
  Reger, D. L.; Leitner, A.; Smith, M. D. Cryst. Growth Des. 2015, 15, 5637. doi: 10.1021/acs.cgd.5b01387
10. [10]
  Pischel, U.; Uzunova, V. D.; Remon, P.; Nau, W. M. Chem. Commun. 2010, 46, 2635. doi: 10.1039/b927595a
11. [11]
  Ferreira, R.; Baleizao, C.; Munõz-Molina, J. M.; BerberanSantos, M. N.; Pischel, U. J. Phys. Chem. A 2011, 115, 1092. doi: 10.1021/jp110470h
12. [12]
  Nandhikonda, P.; Begaye, M. P.; Heagy, M. D. Tetrahedron Lett. 2009, 50, 2459. doi: 10.1016/j.tetlet.2009.02.197
13. [13]
  Jiang, G.; Wang, S.; Yuan, W.; Jiang, L.; Song, Y.; Tian, H.; Zhu, D.-B. Chem. Mater. 2006, 18, 235. doi: 10.1021/cm052251i
14. [14]
  Gu, P.-Y.; Lu, C.-J.; Ye, F.-L.; Ge, J.-F.; Xu, Q.-F.; Hu, Z.-J.; Li, N.-J.; Lu, J.-M. Chem. Commun. 2012, 48, 10234. doi: 10.1039/c2cc35266d
15. [15]
  Borisova, N. E.; Reshetova, M. D.; Ustynyuk, U. Y. Chem. Rev. 2007, 107, 46. doi: 10.1021/cr0683616
16. [16]
  Kamiya, Y.; Asanuma, H. Acc. Chem. Res. 2014, 47, 1663. doi: 10.1021/ar400308f
17. [17]
  Song, Q.-S.; Zhou, W.; Wu, X.-M.; Wu, F. Acta Chim. Sinica 2016, 74, 435 (in Chinese).
18. [18]
  Narayanaswamy, N.; Govindaraju, T. Sens. Actuators, B 2012, 161, 304. doi: 10.1016/j.snb.2011.10.036
19. [19]
  Chereddy, N.; Raju, M.; Nagaraju, P.; Krishnaswamy, V.; Korrapati, P.; Bangal, P.; Rao, V. Analyst 2014, 139, 6352. doi: 10.1039/C4AN01528B
20. [20]
  Bonda, D.; Lee, H.; Blair, J.; Zhu, X.; Perry, G.; Smith, M. Metallomics 2011, 3, 267. doi: 10.1039/c0mt00074d
21. [21]
  Gao, B.; Gong, W.-T.; Zhang, L.-Q.; Ye, J.-W.; Ning, G. Sens. Actuators, B 2012, 162, 391. doi: 10.1016/j.snb.2011.12.060
22. [22]
  Zhang, Y.-M.; Lin, Q.; Wei, T.-B.; Wang, D.-D.; Yao, H.; Wang, Y.-L. Chem. Commun. 2009, 447.
23. [23]
  Chen, C.; Wang, R.-Y.; Guo, L.-Q.; Fu, N.-Y. Org. Lett. 2011, 13, 1162. doi: 10.1021/ol200024g
24. [24]
  Lin, Q.; Zheng, F.; Liu, L.; Mao, P.-P.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. RSC Adv. 2016, 6, 111928. doi: 10.1039/C6RA23878E
25. [25]
  Lin, Q.; Lu, T.-T.; Zhu, X.; Wei, T.-B.; Li, H.; Zhang, Y.-M. Chem. Sci. 2016, 7, 5341. doi: 10.1039/C6SC00955G
26. [26]
  Lin, Q.; Lu, T.-T.; Zhu, X.; Sun, B.; Yang, Q.-P.; Wei, T.-B.; Zhang, Y.-M. Chem. Commun. 2015, 51, 1635. doi: 10.1039/C4CC07814D
27. [27]
  Wei, T.-B.; Chen, J.-F.; Cheng, X.-B.; Li, H.; Han, B.-B.; Zhang, Y.-M.; Yao, H.; Lin, Q. Org. Chem. Front. 2017, 4, 210. doi: 10.1039/C6QO00569A
28. [28]
  Lin, Q.; Sun, B.; Yang, Q.-P.; Fu, Y.-P.; Zhu, X.; Wei, T.-B.; Zhang, Y.-M. Chem.-Eur. J. 2014, 20, 11457. doi: 10.1002/chem.v20.36
29. [29]
  Cheng, X.-B.; Li, H.; Zheng, F.; Lin, Q.; Yao, H.; Zhang, Y.-M.; Wei, T.-B. RSC Adv. 2016, 6, 20987. doi: 10.1039/C5RA26240B
30. [30]
  Lin, Q.; Zhong, K-P.; Zhu, J-H.; Ding, L.; Su, J-X.; Yao, H.; Wei, T.-B.; Zhang, Y.-M. Macromolecule 2017, 50, 7863. doi: 10.1021/acs.macromol.7b01835
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Synthesis and Fe3+ Sensing Properties of the Chemosensor Based on Functionalized Naphthalimide Schiff Base Derivative

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Synthesis and Fe³⁺ Sensing Properties of the Chemosensor Based on Functionalized Naphthalimide Schiff Base Derivative