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
1. [1]
  Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe³⁺ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402
2. [2]
  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
3. [3]
  Yu BAI , Jijiang WANG , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A cadmium(Ⅱ) coordination polymer based on a semirigid tetracarboxylate ligand for highly selective detection of Fe³⁺ and 4-nitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1217-1226. doi: 10.11862/CJIC.20240457
4. [4]
  Pingping LU , Shuguang ZHANG , Peipei ZHANG , Aiyun NI . Preparation of zinc sulfate open frameworks based probe materials and detection of Pb²⁺ and Fe³⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 959-968. doi: 10.11862/CJIC.20240411
5. [5]
  Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
6. [6]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
7. [7]
  Yuanyu YANG , Jianhua XUE , Yujia BAI , Lulu CUI , Dongdong YANG , Qi MA . Design, synthesis, and detection of Al³⁺ of two zinc complexes based on Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1207-1216. doi: 10.11862/CJIC.20250005
8. [8]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
9. [9]
  Qiaoqiao BAI , Anqi ZHOU , Xiaowei LI , Tang LIU , Song LIU . Construction of pressure-temperature dual-functional flexible sensors and applications in biomedicine. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2259-2274. doi: 10.11862/CJIC.20240128
10. [10]
  Yang Meiqing , Lu Wang , Haozi Lu , Yaocheng Yang , Song Liu . Recent Advances of Functional Nanomaterials for Screen-Printed Photoelectrochemical Biosensors. Acta Physico-Chimica Sinica, 2025, 41(2): 2310046-0. doi: 10.3866/PKU.WHXB202310046
11. [11]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
12. [12]
  Yanqiong Wang , Yaqi Hou , Fengwei Huo , Xu Hou . Fe³⁺ ion quantification with reusable bioinspired nanopores. Chinese Chemical Letters, 2025, 36(2): 110428-. doi: 10.1016/j.cclet.2024.110428
13. [13]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
14. [14]
  Jiarong Feng , Yejie Duan , Chu Chu , Dezhen Xie , Qiu'e Cao , Peng Liu . Preparation and Application of a Streptomycin Molecularly Imprinted Electrochemical Sensor: A Suggested Comprehensive Analytical Chemical Experiment. University Chemistry, 2024, 39(8): 295-305. doi: 10.3866/PKU.DXHX202401016
15. [15]
  Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020
16. [16]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . Thickness-Insensitive, Cyano-Modified Perylene Diimide Derivative as a Cathode Interlayer Material for High-Efficiency Organic Solar Cells. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-0. doi: 10.3866/PKU.WHXB202406007
17. [17]
  Ke Zhao , Zhen Liu , Luyao Liu , Changyuan Yu , Jingshun Pan , Xuguang Huang . Functionalized Reflective Structure Fiber-Optic Interferometric Sensor for Trace Detection of Lead Ions. Acta Physico-Chimica Sinica, 2024, 40(4): 2304029-0. doi: 10.3866/PKU.WHXB202304029
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]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
20. [20]
  Lin′an CAO , Dengyue MA , Gang XU . Research advances in electrically conductive metal-organic frameworks-based electrochemical sensors. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 1953-1972. doi: 10.11862/CJIC.20250160

Get Citation

PDF

XML

Metrics

PDF Downloads(22)
Abstract views(2057)
HTML views(717)

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

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

Metrics

通讯作者: 陈斌, bchen63@163.com

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