A Novel Salicylaldehyde Schiff-base Fluorescent Probe for Selective Detection of Cu2+Ion
- Corresponding author: Lin YUAN, tcyl431102@163.com
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
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
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
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
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 S2–. Sensor Actuat. B-Chem. 2019, 280, 129–137.
doi: 10.1016/j.snb.2018.10.038
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
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
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
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
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
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
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.
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
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
Chen, W. T. Structure, photophysical and electrochemical properties of a copper porphyrin with a three-dimensional framework. Acta Crystallogr. C 2020, 76, 133–138.
Lodeiro, C.; Pina, F. Luminescent and chromogenic molecular probes based on polyamines and related compounds. Coord. Chem. Rev. 2009, 253, 1353–1383.
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.
Bruker: APEX3, SAINT-Plus, XPREP. Bruker AXS Inc., USA 2016.
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.
Sheldrick, G. M. SHELXS-97, Program for X-ray Crystal Structure Solution. University of Göttingen, Germany 1997.
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.
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
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
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
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