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-.
  • 加载中
    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

  • 加载中
    1. [1]

      Jinlong YANWeina WUYuan 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

    2. [2]

      Jingjie Tang Luying Xie Jiayu Liu Shangyu Shi Xinyu Sun Jiayang Lin Qikun Yang Chuan'ang Yu Zecheng Wang Yingying Wang Zengyang Xie . Efficient Rapid Synthesis and Antibacterial Activities of Tosylhydrazones: A Recommended Innovative Chemistry Experiment for Undergraduate Medical University. University Chemistry, 2024, 39(3): 316-326. doi: 10.3866/PKU.DXHX202309091

    3. [3]

      Peiran ZHAOYuqian LIUCheng HEChunying DUAN . A functionalized Eu3+ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355

    4. [4]

      Ruiying WANGHui WANGFenglan CHAIZhinan ZUOBenlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052

    5. [5]

      Hong CAIJiewen WUJingyun LILixian CHENSiqi XIAODan LI . Synthesis of a zinc-cobalt bimetallic adenine metal-organic framework for the recognition of sulfur-containing amino acids. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 114-122. doi: 10.11862/CJIC.20240382

    6. [6]

      Yuyao Wang Zhitao Cao Zeyu Du Xinxin Cao Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014

    7. [7]

      Fei Liu Dong-Yang Zhao Kai Sun Ting-Ting Yu Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047

    8. [8]

      Jiaxun Wu Mingde Li Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098

    9. [9]

      Caixia Lin Ting Liu Zhaojiang Shi Hong Yan Keyin Ye Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107

    10. [10]

      Shahua Huang Xiaoming Guo Lin Lin Guangping Chang Sheng Han Zuxin Zhou . Application of “Integration of Industry and Education” in Engineering Chemistry: Improvement of the Pesticide Fipronil Production. University Chemistry, 2024, 39(3): 199-204. doi: 10.3866/PKU.DXHX202309064

    11. [11]

      Aidang Lu Yunting Liu Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029

    12. [12]

      Lina Guo Ruizhe Li Chuang Sun Xiaoli Luo Yiqiu Shi Hong Yuan Shuxin Ouyang Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al2O3催化剂光热催化CO2甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002

    13. [13]

      Yujia LITianyu WANGFuxue WANGChongchen WANG . Direct Z-scheme MIL-100(Fe)/BiOBr heterojunctions: Construction and photo-Fenton degradation for sulfamethoxazole. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 481-495. doi: 10.11862/CJIC.20230314

    14. [14]

      Lirui Shen Kun Liu Ying Yang Dongwan Li Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035

    15. [15]

      Tianlong Zhang Rongling Zhang Hongsheng Tang Yan Li Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006

    16. [16]

      Yikai Wang Xiaolin Jiang Haoming Song Nan Wei Yifan Wang Xinjun Xu Cuihong Li Hao Lu Yahui Liu Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007

    17. [17]

      Yi DINGPeiyu LIAOJianhua JIAMingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393

    18. [18]

      Yuan GAOYiming LIUChunhui WANGZhe HANChaoyue FANJie QIU . A hexanuclear cerium oxo cluster stabilized by furoate: Synthesis, structure, and remarkable ability to scavenge hydroxyl radicals. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 491-498. doi: 10.11862/CJIC.20240271

    19. [19]

      Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020

    20. [20]

      Guoze Yan Bin Zuo Shaoqing Liu Tao Wang Ruoyu Wang Jinyang Bao Zhongzhou Zhao Feifei Chu Zhengtong Li Yusuke Yamauchi Saad Melhi Xingtao Xu . Opportunities and Challenges of Capacitive Deionization for Uranium Extraction from Seawater. Acta Physico-Chimica Sinica, 2025, 41(4): 100032-. doi: 10.3866/PKU.WHXB202404006

Metrics
  • PDF Downloads(2)
  • Abstract views(1622)
  • HTML views(845)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return