Citation: ZHANG Chenglu, LI Yizheng, LI Jinchi, WANG Jing, WANG Huayu, GONG Rongqing. Synthesis of Two Novel 1, 3-Selenazole Carbonyl Hydrazones and Their Specific Fluorescent Recognition Toward Acetate Ions[J]. Chinese Journal of Applied Chemistry, ;2018, 35(2): 197-205. doi: 10.11944/j.issn.1000-0518.2018.02.170129 shu

Synthesis of Two Novel 1, 3-Selenazole Carbonyl Hydrazones and Their Specific Fluorescent Recognition Toward Acetate Ions

  • Corresponding author: ZHANG Chenglu, zhangchenglu@lnnu.edu.cn
  • Received Date: 24 April 2017
    Revised Date: 28 June 2017
    Accepted Date: 11 July 2017

    Fund Project: Technology Research Program of Liaoning Provincial Department of Education 2009A426Supported by Technology Research Program of Liaoning Provincial Department of Education(No.2009A426)

Figures(10)

  • Two novel 1, 3-selenazole carbonyl hydrazones(SAF1, SAF2) were synthesized and their structures were confirmed by infrared spectrometry and nuclear magnetic resonance. Monitoring of nine common anions using probes SAF1 and SAF2 was performed via ultraviolet-visible and fluorescent spectra. When acetate ions(AcO-) were added, a new absorption peak of SAF1 and SAF2 was found at 500 nm and 414 nm, respectively. The color of SAF1 and SAF2 solutions changed from pale yellow to red and yellow, respectively. These results show naked eye identification of AcO-. In fluorescent spectra, a strong emission peak at 417 nm is found with the turn-on effect. The lowest limit of detection for AcO- reaches 10-5 mol/L. The binding constants of SAF1 and SAF2 with AcO- are 3.03×104 and 1.42×104 L/mol, respectively. SAF1 and SAF2 are expected to be specific fluorescent probes toward AcO-.
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    1. [1]

      Jiang Y, Sun L L, Ren G Z. A Novel Colorimetric and Fluorescent Iminocoumarin-Based Chemosensor for Acetate Ion and Its Application to Living Cell Imaging[J]. Talanta, 2016,146(1):732-736.  

    2. [2]

      Yang S, Yin B, Xu L. A Natural Quercetin-Based Fluorescent Sensor for Highly Sensitive and Selective Detection of Copper Ions[J]. Anal Methods, 2015,7(11):4546-4551. doi: 10.1039/C5AY00375J

    3. [3]

      Gupta V K, Singh A K, Bhardwaj S. Biological Active Novel 2, 4-Dinitro Phenyl Hydrazones as the Colorimetric Sensors for Selective Detection of Acetate Ion[J]. Sens Actuators B, 2014,197(5):264-273.  

    4. [4]

      Zhao H C, Shi Y P, Liu Y M. Synthesis and Antitumor-Evaluation of 1, 3-Selenazole-Containing 1, 3, 4-Thiadiazole Derivatives[J]. Bioorg Med Chem Lett, 2013,23(24):6577-6579.  

    5. [5]

      ZHANG Chenglu, GUO Yang, CHEN Ying. Synthesis and Properties of Novel Tripod Type Multi-benzimidazole Quaternary Ammonium Compounds[J]. Chinese J Org Chem, 2015,35(8):1665-1672.  

    6. [6]

      Sun Y, Liu Y, Guo W. Fluorescent and Chromogenic Probes Bearing Salicylaldehyde Hydrazone Functionality for Cyanide Detection in Aqueous Solution[J]. Sen Actuators B, 2009,143(1):171-176. doi: 10.1016/j.snb.2009.09.038

    7. [7]

      Sun Y, Liu Y, Chen M. A Novel Fluorescent and Chromogenic Probe for Cyanide Detection in Water Based on the Nucleophilic Addition of Cyanide to Imine Group[J]. Talanta, 2009,80(2):996-1000. doi: 10.1016/j.talanta.2009.08.026

    8. [8]

      Madhuprasad A, Nityananda S. Colorimetric Receptors for Naked Eye Detection of Inorganic Fluoride Ion in Aqueous Media Using ICT Mechanism[P]. RSC Adv, 2012, 2: 10499-10504.

    9. [9]

      Bai B L, Ma J, Wei J. A Simple Structural Hydrazide-Based Gelator as a Fluoride Ion Colorimetric Sensor[J]. Org Biomol Chem, 2014,12:3478-3483. doi: 10.1039/c4ob00056k

    10. [10]

      ZHANG Zhou, LI Yaochang, FAN Wangxi. Research Progress of Acylhydrazone Compounds[J]. Anhui Agric Sci, 2010,38(13):6644-6645.  

    11. [11]

      Cenzo C, Valentina O. Synthesis and Biological Evaluation of Novel Acylhydrazone Derivatives as Potential Antitumor Agents[J]. Bioorg Med Chem, 2013,21(21):6592-6599. doi: 10.1016/j.bmc.2013.08.026

    12. [12]

      Li J R, Li D D, Wang R R. Design and Synthesis of Thiazole Derivatives as Potent FabH Inhibitors with Antibacterial Activity[J]. Eur J Med Chem, 2014,75(21):438-447.  

    13. [13]

      Liu Q, Zhang X, He Y. Oxidative Rearrangement Strategy for Synthesis of 2, 4, 5-Trisubstituted Oxazoles Utilizing Hypervalent Iodine Reagent[J]. Tetrahedron, 2016,72(38):5749-5753. doi: 10.1016/j.tet.2016.07.082

    14. [14]

      Aristi P, Valentina G. Selenium Compounds as Therapeutic Agents in Cancer[J]. Biochim Biophys Acta, 2014,1850(8):1642-1660.  

    15. [15]

      Ninomiya M, Garud D R, Koketsu M. Biologically Significant Selenium-Containing Heterocycles[J]. Coord Chem Rev, 2011,255(23):2968-2990.  

    16. [16]

      Suzanne F, Stephen J E, Anthony F H. Nitrile Ylide Dimerization:Investigation of the Carbene Reactivity of Nitrile Ylides[J]. J Org Chem, 2004,69(14):4663-4669. doi: 10.1021/jo049748g

    17. [17]

      Hua G, Li Y, Slawin A M Z. Synthesis of Primary Arylselenoamides by Reaction of Aryl Nitriles with Woollins' Reagent[J]. Org Lett, 2006,8(23):5251-5254. doi: 10.1021/ol062053c

    18. [18]

      Shao J, Lin H, Cai Z S. A Simple Colorimetric and ON-OFF Fluorescent Chemosensor for Biologically Important Anions Based on Amide Moieties[J]. J Photochem Photobiol B, 2009,95(1):1-5.  

    19. [19]

      LIU Yanghong, LIU Ge. Synthesis of a Novel Acylhydrazone Receptor and Its Anion Recognition Properties[J]. Chem Reag, 2012,34(3):253-256.  

    20. [20]

      Ivan V K, Mimi C, Phillip L B. Anion Binding to Monotopic and Ditopic Macrocyclic Amides[J]. Org Lett, 2006,8(15):3171-3174. doi: 10.1021/ol060786r

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