Citation: WU Xin, MA Jun, NAN Ming, SHUANG Shaomin, DONG Chuan. Synthesis of a Fluorescein Derivative 5-Bromosalicylicaldehyde Fluorescein Hydrazone and the Detection for Copper(Ⅱ) Ion[J]. Chinese Journal of Applied Chemistry, ;2016, 33(3): 357-363. doi: 10.11944/j.issn.1000-0518.2016.03.150238 shu

Synthesis of a Fluorescein Derivative 5-Bromosalicylicaldehyde Fluorescein Hydrazone and the Detection for Copper(Ⅱ) Ion

WU Xin ^a,b ,
MA Jun ^a ,
NAN Ming ^a ,
SHUANG Shaomin ^a ,
DONG Chuan ^a,,

a.
a. Institute of Environmental Science, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China;
b.
b. School of Arts and Sciences, Shanxi Agricultural University, Taigu, Shanxi 030801, China

Corresponding author: DONG Chuan,
Received Date: 9 July 2015
Available Online: 23 October 2015
Fund Project:

A novel fluorescein derivative, 5-bromosalicylicaldehyde fluorescein hydrazone(BSFH), has been synthesized by reacting fluorescein hydrazine with 5-bromosalicylicaldehyde and characterized by IR, NMR, MS, elemental analysis. The selectivity of BSFH to common metal ions in aqueous solution was investigated by absorption spectroscopy. BSFH has almost no absorption in visible region and very low absorption at 496 nm with addition of other metal ions except Cu²⁺. However, in the presence of Cu²⁺, a rapid color change of BSFH from colorless to yellow along with a very obvious absorption appears at 496 nm in the absorption spectrum. The absorbance of BSFH at 496 nm increases gradually with the increase of Cu²⁺. The selective binding of BSFH to Cu²⁺ over other metal ions is remarkably high in the aqueous solution. Experimental results indicate that the chemical stoichiometric ratio between BSFH and Cu²⁺ is 1:1, the linear range of detecting Cu²⁺ concentration is 0.30~10 μmol/L, common metal ions do not show any interference on the determination of Cu²⁺, the detection limit is 0.30 μmol/L, and BSFH is highly sensitive to Cu²⁺ in the aqueous solution. Therefore, BSFH can be utilized to detect Cu²⁺ at low concentration with simple, rapid and sensitive method.
- fluorescein derivative,
- bromosalicylicaldehyde fluorescein hydrazone,
- cupper(Ⅱ) ion,
- absorption spectrum,
- detection
1. [1]
  [1] Egawa T,Koide Y,Hanaoka K,et al. Development of a Fluorescein Analogue, TokyoMagenta, as a Novel Scaffold for Fluorescence Probes in Red Region[J]. Chem Commun,2011,47:4162-4164.
2. [2]
  [2] Li T,Yang Z,Li Y,et al. A Novel Fluorescein Derivative as a Colorimetric Chemosensor for Detecting Copper(Ⅱ) Ion[J]. Dyes Pigm,2011,88(1):103-108.
3. [3]
  [3] Huo F J,Yin C X,Yang Y T,et al. Ultraviolet-visible Light(UV-Vis)-reversible but Fluorescence-irreversible Chemosensor for Copper in Water and Its Application in Living Cells[J]. Anal Chem,2012,84(5):2219-2223.
4. [4]
  [4] Jin X,Hao L,Hu Y,et al. Two Novel Fluorescein-based Fluorescent Probes for Hypochlorite and Its Real Applications in Tap Water and Biological Imaging[J]. Sens Actuators,B,2013,186:56-60.
5. [5]
  [5] Zhang X,Zhang Y,Zhu Z. A Fluorescein Semicarbazide-based Fluorescent Probe for Highly Selective and Rapid Detection of Hypochlorite in Aqueous Solution[J]. Anal Methods,2012,4:4334.
6. [6]
  [6] Ma X,Liu C,Shan Q,et al. A Fluorescein-based Probe with High Selectivity and Sensitivity for Sulfite Detection in Aqueous Solution[J]. Sens Actuators,B,2013,188:1196-1200.
7. [7]
  [7] Yang X F,Wang L,Xu H,et al. A Fluorescein-based Fluorogenic and Chromogenic Chemodosimeter for the Sensitive Detection of Sulfide Anion in Aqueous Solution[J]. Anal Chim Acta,2009,631(1):91-95.
8. [8]
  [8] Huo F J,Zhang J J,Yang Y T,et al. A Fluorescein-based Highly Specific Colorimetric and Fluorescent Probe for Hypochlorites in Aqueous Solution and Its Application in Tap Water[J]. Sens Actuators,B,2012,166/167:44-49.
9. [9]
  [9] Yang X F,Li Y,Bai Q. A Highly Selective and Sensitive Fluorescein-based Chemodosimeter for Hg²⁺ Ions in Aqueous Media[J]. Anal Chim Acta,2007,584(1):95-100.
10. [10]
  [10] Muthuraj B,Deshmukh R,Trivedi V,et al. Highly Selective Probe Detects Cu²⁺ and Endogenous NO Gas in Living Cell[J]. ACS Appl Mater Interfaces,2014,6(9):6562-6569.
11. [11]
  [11] Kulchat S,Chaicham A,Ekgasit S,et al. Self-assembled Coordination Nanoparticles from Nucleotides and Lanthanide Ions with Doped-boronic Acid-fluorescein for Detection of Cyanide in the Presence of Cu in Water[J]. Talanta,2012,89:264-269.
12. [12]
  [12] Hyman L M,Stephenson C J,Dickens M G,et al. Toward the Development of Prochelators as Fluorescent Probes of Copper-mediated Oxidative Stress[J]. Dalton Trans,2010,39(2):568-576.
13. [13]
  [13] Chen X T,Li Z F,Xiang Y,et al. Salicylaldehyde Fluorescein Hydrazone:A Colorimetric Logic Chemosensor for pH and Cu(Ⅱ)[J]. Tetrahedron Lett,2008,49(32):4697-4700.
14. [14]
  [14] Jiang L,Wang L,Guo M,et al.Fluorescence Turn-on of Easily Prepared Fluorescein Derivatives by Zinc Cation in Water and Living Cells[J]. Sens Actuators,B,2011,156(2):825-831.
15. [15]
  [15] Zhang J,Zhang L,Wei Y,et al. A Selectively Fluorescein-based Colorimetric Probe for Detecting Copper(Ⅱ) Ion[J]. Spectrochim Acta,Part A,2014,122:731-736.
16. [16]
  [16] Yang Y,Huo F,Yin C,et al.Combined Spectral Experiment and Theoretical Calculation to Study the Chemosensors of Copper and Their Applications in Anion Bioimaging[J]. Sens Actuators,B,2013,177:1189-1197.
17. [17]
  [17] Que E L,Domaille D W ,Chang C J. Metals in Neurobiology:Probing Their Chemistry and Biology with Molecular Imaging[J]. Chem Rev,2008,108(5):1517-1549.
18. [18]
  [18] YUE Kong,XIA Yan. Review on Study About Untidecay Treatment in Wood[J]. Wood Process Machin,2007,(6):50-53(in Chinese).岳孔,夏炎.木质材料防腐朽菌败坏研究综述[J]. 木材加工机械,2007,(6):50-53.
19. [19]
  [19] Qu L J,Yin C X,Huo F J,et al. A Pyridoxal-based Dual Chemosensor for Visual Detection of Copperion and Ratiometric Fluorescent Detection of Zinc Ion[J]. Sens Actuators,B,2014,191:158-164.
20. [20]
  [20] YUAN Yuehua,TIAN Maozhong,FENG Feng,et al.Rhodamine-Based Fluorescent Probes for Cations[J]. Prog Chem,2010,22(10):1929-1939(in Chinese).袁跃华,田茂忠,冯峰,等. 罗丹明类阳离子荧光探针[J]. 化学进展,2010,22(10):1929-1939.
21. [21]
  [21] Wuhan University. Analytical Chemistry[M]. 5nd Ed. Beijing:China Higher Education Press,2007:11-13(in Chinese).武汉大学. 分析化学[M]. 第5版. 北京:高等教育出版社,2007:11-13.
22. [22]
  [22] Zhang L,Zhang X. A Selectively Fluorescein-based Colorimetric Probe for Detecting Copper(Ⅱ) Ion[J]. Spectrochim Acta,Part A,2014,133:54-59.
1. [1]
  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
2. [2]
  Hao BAI , Weizhi JI , Jinyan CHEN , Hongji LI , Mingji LI . Preparation of Cu₂O/Cu-vertical graphene microelectrode and detection of uric acid/electroencephalogram. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1309-1319. doi: 10.11862/CJIC.20240001
3. [3]
  Mengyao Shi , Kangle Su , Qingming Lu , Bin Zhang , Xiaowen Xu . Determination of Potassium Content in Tobacco Stem Ash by Flame Atomic Absorption Spectroscopy. University Chemistry, 2024, 39(10): 255-260. doi: 10.12461/PKU.DXHX202404105
4. [4]
  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
5. [5]
  Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . S型ZnO/CdIn₂S₄光催化剂制备H₂O₂偶联苄胺氧化的超快电子转移飞秒吸收光谱研究. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-. doi: 10.1016/j.actphy.2025.100064
6. [6]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
7. [7]
  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
8. [8]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
9. [9]
  Liwei Wang , Guangran Ma , Li Wang , Fugang Xu . A Comprehensive Analytical Chemistry Experiment: Colorimetric Detection of Vitamin C Using Nanozyme and Smartphone. University Chemistry, 2024, 39(8): 255-262. doi: 10.3866/PKU.DXHX202312094
10. [10]
  Qin Hou , Jiayi Hou , Aiju Shi , Xingliang Xu , Yuanhong Zhang , Yijing Li , Juying Hou , Yanfang Wang . Preparation of Cuprous Iodide Coordination Polymer and Fluorescent Detection of Nitrite: A Comprehensive Chemical Design Experiment. University Chemistry, 2024, 39(8): 221-229. doi: 10.3866/PKU.DXHX202312056
11. [11]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
12. [12]
  Yi Li , Zhaoxiang Cao , Peng Liu , Xia Wu , Dongju Zhang . Revealing the Coloration and Color Change Mechanisms of the Eriochrome Black T Indicator through Computational Chemistry and UV-Visible Absorption Spectroscopy. University Chemistry, 2025, 40(3): 132-139. doi: 10.12461/PKU.DXHX202405154
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
17. [17]
  Jinghan ZHANG , Guanying CHEN . Progress in the application of rare-earth-doped upconversion nanoprobes in biological detection. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2335-2355. doi: 10.11862/CJIC.20240249
18. [18]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
19. [19]
  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
20. [20]
  Chun-Lin Sun , Yaole Jiang , Yu Chen , Rongjing Guo , Yongwen Shen , Xinping Hui , Baoxin Zhang , Xiaobo Pan . Construction, Performance Testing, and Practical Applications of a Home-Made Open Fluorescence Spectrometer. University Chemistry, 2024, 39(5): 287-295. doi: 10.3866/PKU.DXHX202311096

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(434)
HTML views(65)

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