Citation: Yuan-Da LI, Jin-Hao KUANG, Hai-Bo QIN, Ke-Xiang LIU, Xu FAN, Zhong-Yan LI, Lin YUAN. A Novel Salicylaldehyde Schiff-base Fluorescent Probe for Selective Detection of Cu²⁺Ion[J]. Chinese Journal of Structural Chemistry, ;2022, 41(3): 220313. doi: 10.14102/j.cnki.0254-5861.2011-3288 shu

A Novel Salicylaldehyde Schiff-base Fluorescent Probe for Selective Detection of Cu²⁺Ion

Hunan University of Science and Engineering, Yongzhou 425199, China

Corresponding author: Lin YUAN, tcyl431102@163.com
Received Date: 19 June 2021
Accepted Date: 3 September 2021

Fund Project: the Natural Science Foundation of Hunan Province 2021JJ30291Undergraduate Training Program for Innovation and Entrepreneurship of Hunan Province [2021]197-3585Undergraduate Training Program for Innovation and Entrepreneurship of Hunan University of Science and Engineering 2021

Figures(8)

A novel Schiff-base fluorescent probe 6, 6'-((1E, 1'E)-(ethane-1, 2-diylbis(azaneylylidene))bis-(methaneylylidene))bis(3-(diethylamino)phenol) (L) was derived from the 2:1 M condensation of 4-(diethylamino)-2-hydroxybenzaldehyde with ethylenediamine and characterized by ¹H NMR, ¹³C NMR and FT-IR spectroscopies. The results of spectral analysis showed that the probe L is selective and sensitive to Cu²⁺. The detection limit of L is found to be 19 nmol·L^-1. There is a good linear relationship between the fluorescence intensity of probe L and the concentration of Cu²⁺ in the range of 0 to 20 μmol·L^-1. X-ray crystal structure of the L-Cu²⁺ complex and the Job plot revealed a 1:1 L-Cu²⁺ identification.
- Cu²⁺,
- salicylaldehyde,
- Schiff-base,
- fluorescent probe
1. [1]
  Zhu, Y. M.; Wang, Z. L.; Yang, J.; Xu, X.; Wang, S. F.; Cai, Z. C.; Xu, H. J. N, N-bis(2-pyridylmethyl)amine-based truxene derivative as a highly sensitive fluorescence sensor for Cu²⁺ and Ni²⁺ ion. Chin. J. Org. Chem. 2019, 39, 427–433. doi: 10.6023/cjoc201807042
2. [2]
  Tachapermpon, Y.; Chaneam, S.; Charoenpanich, A.; Sirirak, J.; Wanichacheva, N. Highly Cu²⁺ sensitive and selective colorimetric and fluorescent probes: utilizations in batch, flow analysis and living cell imaging. Sensor Actuat. B-Chem. 2017, 241, 868–879. doi: 10.1016/j.snb.2016.11.009
3. [3]
  Meng, X. J.; Zhao, J. Z.; Ma, W. B. Progress in fluorescent probes for Cu²⁺ and anions, neutral molecules sequential recognition. Chin. J. Org. Chem. 2020, 40, 276–283. doi: 10.6023/cjoc201908039
4. [4]
  Xu, J. B.; Liu, N.; Hao, C. W.; Han, Q. Q.; Duan, Y. L.; Wu, J. A novel fluorescence "on-off-on" peptide-based chemosensor for simultaneous detection of Cu²⁺, Ag⁺ and S^2–. Sensor Actuat. B-Chem. 2019, 280, 129–137. doi: 10.1016/j.snb.2018.10.038
5. [5]
  Barnham, K. J.; Masters, C. L.; Bush, A. L. Neurodegenerative diseases and oxidative stress. Nat. Rev. Drug Discov. 2004, 3, 205–214. doi: 10.1038/nrd1330
6. [6]
  Zeng, L.; Miller, E. W.; Pralle, A.; Isacoff, E. Y.; Chang, C. J. A selective turn-on fluorescent sensor for imaging copper in living cells. J. Am. Chem. Soc. 2006, 128, 10–11. doi: 10.1021/ja055064u
7. [7]
  Carter, K. P.; Young, A. M.; Palmer, A. E. Fluorescent sensors for measuring metal ions in living systems. Chem. Rev. 2014, 114, 4564–4601. doi: 10.1021/cr400546e
8. [8]
  Zhang, B. B.; Qin, F. Y.; Niu, H. W.; Liu, Y.; Zhang, D.; Ye, Y. A highly sensitive and fast responsive naphthalimide-based fluorescent probe for Cu²⁺ and its application. New J. Chem. 2017, 41, 14683–14688. doi: 10.1039/C7NJ02813J
9. [9]
  Tang, J.; Ma, S. G.; Zhang, D.; Liu, Y. Q.; Zhao, Y. F.; Ye, Y. Highly sensitive and fast responsive ratiometric fluorescent probe for Cu²⁺ based on a naphthalimide-rhodamine dyad and its application in living cell imaging. Sensor Actuat. B-Chem. 2016, 236, 109–115. doi: 10.1016/j.snb.2016.05.144
10. [10]
  Cai, F. J.; Xia, F.; Guo, Y. X.; Zhu, W. H.; Fu, B.; Liang, X.; Wang, S. F.; Cai, Z. C.; Xu, H. J. "Off-on-off" type of selectively pH-sensing 8-hydroxyquinoline-substituted gallium(III) corrole. New J. Chem. 2019, 43, 18012–18017. doi: 10.1039/C9NJ04544A
11. [11]
  Tao, J. Y.; Song, W. T.; Sun, L.; Li, Z. Z.; Fu, B.; Cai, Z. C.; Xu, H. J. Synthesis, photo-physical properties and cell imaging of meso-2, 6-dichlorophenyl boron-dipyrromethene derivatives. Chin. J. Struct. Chem. 2019, 38, 1503–1510.
12. [12]
  Saura, A. V.; Burguete, M. I.; Galindo, F.; Luis, S. V. Novel fluorescent anthracene-bodipy dyads displaying sensitivity to pH and turn-on behaviour towards Cu(II) ions. Org. Biomol. Chem. 2017, 15, 3013–3024. doi: 10.1039/C7OB00274B
13. [13]
  Song, Y. T.; Tao, J. Y.; Wang, Y.; Cai, Z. C.; Fang, X. Y.; Wang, S. F.; Xu, H. J. A novel dual-responsive fluorescent probe for the detection of copper(II) and nickel(II) based on BODIPY derivatives. Inorg. Chim. Acta 2021, 516, 120099–7. doi: 10.1016/j.ica.2020.120099
14. [14]
  Chen, W. T. Structure, photophysical and electrochemical properties of a copper porphyrin with a three-dimensional framework. Acta Crystallogr. C 2020, 76, 133–138.
15. [15]
  Lodeiro, C.; Pina, F. Luminescent and chromogenic molecular probes based on polyamines and related compounds. Coord. Chem. Rev. 2009, 253, 1353–1383.
16. [16]
  Li, Z. Y.; Jia, G. K.; Yuan, L.; Bai, P. F.; He, H.; Zhou, Q. Syntheses, crystal structures and biological activities of three new Schiff bases derived from substituted salicylaldehyde and tris base. Chin. J. Struct. Chem. 2017, 36, 1792–1802.
17. [17]
  Bruker: APEX3, SAINT-Plus, XPREP. Bruker AXS Inc., USA 2016.
18. [18]
  Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Spagna, R. SIR2004: an improved tool for crystal structure determination and refinement. J. Appl. Crystallogr. 2005, 38, 381–388.
19. [19]
  Sheldrick, G. M. SHELXS-97, Program for X-ray Crystal Structure Solution. University of Göttingen, Germany 1997.
20. [20]
  Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341.
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
5. [5]
  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
6. [6]
  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
7. [7]
  Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
8. [8]
  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
9. [9]
  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
10. [10]
  Wenhao Chen , Muxuan Wu , Han Chen , Lue Mo , Yirong Zhu . Cu₂Se@C thin film with three-dimensional braided structure as a cathode material for enhanced Cu²⁺ storage. Chinese Chemical Letters, 2024, 35(5): 108698-. doi: 10.1016/j.cclet.2023.108698
11. [11]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
12. [12]
  Tao Liu , Xuwei Han , Xueyi Sun , Weijie Zhang , Ke Gao , Runan Min , Yuting Tian , Caixia Yin . An activated fluorescent probe to monitor NO fluctuation in Parkinson’s disease. Chinese Chemical Letters, 2025, 36(3): 110170-. doi: 10.1016/j.cclet.2024.110170
13. [13]
  Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
14. [14]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912
15. [15]
  Linfang Wang , Jing Liu , Minghao Ren , Wei Guo . A highly sensitive fluorescent HClO probe for discrimination between cancerous and normal cells/tissues. Chinese Chemical Letters, 2024, 35(6): 108945-. doi: 10.1016/j.cclet.2023.108945
16. [16]
  Yang Liu , Leilei Zhang , Kaixuan Liu , Ling-Ling Wu , Hai-Yu Hu . Penicillin G acylase-responsive near-infrared fluorescent probe: Unravelling biofilm regulation and combating bacterial infections. Chinese Chemical Letters, 2024, 35(11): 109759-. doi: 10.1016/j.cclet.2024.109759
17. [17]
  Huamei Zhang , Jingjing Liu , Mingyue Li , Shida Ma , Xucong Zhou , Aixia Meng , Weina Han , Jin Zhou . Imaging polarity changes in pneumonia and lung cancer using a lipid droplet-targeted near-infrared fluorescent probe. Chinese Chemical Letters, 2024, 35(12): 110020-. doi: 10.1016/j.cclet.2024.110020
18. [18]
  Pei Huang , Weijie Zhang , Junping Wang , Fangjun Huo , Caixia Yin . Rapid and specific fluorescent probe visualizes dynamic correlation of Cys and HClO in OGD/R. Chinese Chemical Letters, 2025, 36(1): 109778-. doi: 10.1016/j.cclet.2024.109778
19. [19]
  Lanyun Zhang , Weisi Wang , Yu-Qiang Zhao , Rui Huang , Yuxun Lu , Ying Chen , Liping Duan , Ying Zhou . Mechanism study of the molluscicide candidate PBQ on Pomacea canaliculata using a viscosity-sensitive fluorescent probe. Chinese Chemical Letters, 2025, 36(1): 109798-. doi: 10.1016/j.cclet.2024.109798
20. [20]
  Fan Zheng , Runsha Xiao , Shuai Huang , Zhikang Chen , Chen Lai , Anyao Bi , Heying Yao , Xueping Feng , Zihua Chen , Wenbin Zeng . Accurate visualization colorectal cancer by monitoring viscosity variations with a novel mitochondria-targeted fluorescent probe. Chinese Chemical Letters, 2025, 36(2): 109876-. doi: 10.1016/j.cclet.2024.109876

Get Citation

PDF

XML

Metrics

PDF Downloads(16)
Abstract views(813)
HTML views(154)

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

A Novel Salicylaldehyde Schiff-base Fluorescent Probe for Selective Detection of Cu2+Ion

Metrics

通讯作者: 陈斌, bchen63@163.com

A Novel Salicylaldehyde Schiff-base Fluorescent Probe for Selective Detection of Cu²⁺Ion