Citation: Jing-Ya LI, Wen-Ru HUANG, Feng WANG, Yan-Yan ZHOU. Highly sensitive detection of small molecular weight amines based on an amino alcohol modified β-diketonate europium complex[J]. Chinese Journal of Inorganic Chemistry, ;2023, 39(1): 71-79. doi: 10.11862/CJIC.2022.265 shu

Highly sensitive detection of small molecular weight amines based on an amino alcohol modified β-diketonate europium complex

  • Corresponding author: Yan-Yan ZHOU, zhouyanyan@hlju.edu.cn
  • Received Date: 7 June 2022
    Revised Date: 5 October 2022

Figures(10)

  • As a kind of volatile toxic amines, organic small-molecule amines do great harm to human health. Therefore, the detection of organic small-molecule amines has attracted extensive attention. Lanthanide luminescence sensors stand out among all kinds of fluorescent sensors because of their easy synthesis, high biocompatibility, and high sensitivity. However, the large ion radius and unstable coordination configuration of lanthanide ions make it a challenge to achieve high-sensitivity luminescence detection of organic small-molecule amines in the solid state. The mononuclear lanthanide complex [Eu(L)3(H2O)2] (HL=(2Z)-1-(4-(bis(2-hydroxyethyl)amino)phenyl)-4, 4, 4-trifluoro-3-hydroxybut-2-en-1-one) with intraligand charge transfer (ILCT) properties was successfully constructed by the coordination of the mono-β-diketone ligand with the lanthanide ion europium by introducing the amine alcohol recognition group. The sensing study of the complex showed that [Eu(L)3(H2O)2] exhibited obvious luminescence enhancement response to small organic amines such as tripropylamine under weak nucleophilic action.
  • 加载中
    1. [1]

      Mir-Cerda A, Granell B, Izquierdo-Lopart A, Sahuquillo A, Lopez-Sanchez J F, Saurina J, Sentellas S. Data fusion approaches for the characterization of musts and wines based on biogenic amine and elemental composition[J]. Sensors, 2022,222132. doi: 10.3390/s22062132

    2. [2]

      Duan Y X, Lin H, He P H, Chen Q S. Detection of volatile marker in the wheat infected with Aspergillus flavus by porous silica nanospheres doped Bodipy dyes[J]. Sens. Actuator B-Chem., 2021,330129407. doi: 10.1016/j.snb.2020.129407

    3. [3]

      Zhong H T, Xue Y T, Zhang P Y, Liu B, Zhang X, Chen Z B, Li K, Zheng L R, Zuo X. Cascade reaction system integrating nanozymes for colorimetric discrimination of organophosphorus pesticides[J]. Sens. Actuator B-Chem., 2022,350130810. doi: 10.1016/j.snb.2021.130810

    4. [4]

      Bjorkqvist B. Separation and determination of aliphatic and aromatic amines by high-performance liquid chromatography with ultraviolet detection[J]. J. Chromatogr. A, 1981,204:109-114. doi: 10.1016/S0021-9673(00)81645-3

    5. [5]

      Chiavari G, Giumanin A G. Gas chromatographic analysis of aromatic amines as N-permethylated derivatives[J]. J. Chromatogr. A, 1981,206:555-561. doi: 10.1016/S0021-9673(00)88925-6

    6. [6]

      Varney M S, Preson M R. Measurement of trace aromatic amines in seawater using high-performance liquid chromatography with electrochemical detection[J]. J. Chromatogr. A, 1985,348:265-274. doi: 10.1016/S0021-9673(01)92460-4

    7. [7]

      Wang P G, Krynitsky A J. Rapid determination of para-phenylenediamine by gas chromatography-mass spectrometry with selected ion monitoring in henna-containing cosmetic products[J]. J. Chromatogr. B, 2011,879:1795-1801. doi: 10.1016/j.jchromb.2011.04.030

    8. [8]

      Fan L J, Zhang Y, Murphy C B, Angell S E, Parker M F L, Flynn B R, Jones W E. Fluorescent conjugated polymer molecular wire chemosensors for transition metal ion recognition and signaling[J]. Coord. Chem. Rev., 2009,253:410-422. doi: 10.1016/j.ccr.2008.03.008

    9. [9]

      Wu L L, Huang C S, Emery B P, Sedgwick A C, Bull S D, He X P, Tian H, Yoon J Y, Sessler J, James T D. Förster resonance energy transfer (FRET)-based small-molecule sensors and imaging agents[J]. Chem. Soc. Rev., 2020,49:5110-5139. doi: 10.1039/C9CS00318E

    10. [10]

      Yang G H, Zhao J L, Yi S Z, Wan X J, Tang J N. Biodegradable and photostable Nb2C MXene quantum dots as promising nanofluorophores for metal ions sensing and fluorescence imaging[J]. Sens. Actuator B-Chem., 2020,309127735. doi: 10.1016/j.snb.2020.127735

    11. [11]

      Zhao Y J, Kesong M, Zhu Z T, Fan L J. Fluorescence quenching of a conjugated polymer by synergistic amine-carboxylic acid and π -π interactions for selective detection of aromatic amines in aqueous solution[J]. ACS Sens., 2017,2:842-847. doi: 10.1021/acssensors.7b00245

    12. [12]

      Villa I, Vedda A, Cantarelli I X, Pedroni M, Piccinelli F, Bettinelli M, Speghini A, Quintanilla M, Vetrone F, Rocha U, Jacinto C, Carrasco E, Rodríhuez F S, Juarranz Á, Rosal B D, Ortgies D H, Gonzalez P H, Solé J G, García D J. 1[J]. 3μm emitting SrF2: Nd3+ nanoparticles for high contrast in vivo imaging in the second biological window. Nano Res., 2015,8:649-665.

    13. [13]

      Zhang L B, Wang E K. Metal nanoclusters: New fluorescent probes for sensors and bioimaging[J]. Nano Today, 2014,9:132-157. doi: 10.1016/j.nantod.2014.02.010

    14. [14]

      Guo L R, Panderi I, Yan D D, Szulak K, Li Y J, Chen Y T, Ma H, Niesen D B, Seeram N, Ahmed A, Pantazatos D, Lu W. A comparative study of hollow copper sulfide nanoparticles and hollow gold nanospheres on degradability and toxicity[J]. ACS Nano, 2013,7:8780-8793. doi: 10.1021/nn403202w

    15. [15]

      Yang G H, Wan X J, Gu Z P, Zeng X R, Tang J N. Near infrared photothermal -responsive poly(vinyl alcohol)/black phosphorus composite hydrogels with excellent on-demand drug release capacity[J]. J. Mater. Chem. B, 2018,6:1622-1632. doi: 10.1039/C7TB03090H

    16. [16]

      Cidália M G, Harte A J, Quinn S J, Gunnlaugsson T. Recent developments in the field of supramolecular lanthanide luminescent sensors and self-assemblies[J]. Coord. Chem. Rev., 2008,252:2512-2527. doi: 10.1016/j.ccr.2008.07.018

    17. [17]

      Yoo Y J, Ko J H, Kim W G, Kim Y J, Kong D J, Kim S, Oh J W, Song Y M. Dual-mode colorimetric sensor based on ultrathin resonating facilitator capable of nanometer-thick virus detection for environment monitoring[J]. ACS Appl. Nano Mater., 2020,3(7):6636-6644. doi: 10.1021/acsanm.0c01067

    18. [18]

      Yao Y, Zhou Y, Zhu T, Gao T, Li H, Yan P. Eu(Ⅲ) Tetrahedron cage as a luminescent chemosensor for rapidly reversible and turn-on detection of volatile amine/NH 3[J]. ACS Appl. Mater. Interfaces, 2020,12(13):15338-15347. doi: 10.1021/acsami.9b21425

    19. [19]

      Yao Y, Li J Y, Zhou Y Y, Gao T, Li H F, Yan P F. Turn-on luminescence detection of biogenic amine with an Eu (Ⅲ) tetrahedron cage[J]. Dyes Pigment., 2021,192109441. doi: 10.1016/j.dyepig.2021.109441

    20. [20]

      Ilmi R, Khan M S, Li Z Z, Zhou L, Wong W Y, Marken F, Raithby P R. Utilization of ternary europium complex for organic electroluminescent devices and as a sensitizer to improve electroluminescence of red-emitting iridium complex[J]. Inorg. Chem., 2019,58:8316-8331. doi: 10.1021/acs.inorgchem.9b00303

    21. [21]

      Rocha J, Carlos L D, Paz A A F, Ananias D. Luminescent multifunctional lanthanides-based metal-organic frameworks[J]. Chem. Soc. Rev., 2011,40:926-940. doi: 10.1039/C0CS00130A

    22. [22]

      Yang N N, Sun W, Xi F G, Sui Q, Chen L J, Gao E Q. Postsynthetic N-methylation making a metal-organic framework responsive to alkylamines[J]. Chem. Commun., 2017,53:1747-1750. doi: 10.1039/C6CC10278F

    23. [23]

      Zhang W Q, Li Q Y, Cheng J Y, Cheng K, Yang X Y, Li Y W, Zhao X S, Wang X J. Ratiometric luminescent detection of organic amines due to the induced lactam-lactim tautomerization of organic linker in a metal-organic framework[J]. ACS Appl. Mater. Interfaces, 2017,9(37):31352-31356. doi: 10.1021/acsami.7b11125

    24. [24]

      Fredrich S, Bonasera A, Valderrey V, Hecht S. Sensitive assays by nucleophile-induced rearrangement of photoactivated diarylethenes[J]. J. Am. Chem. Soc., 2018,140(20):6432-6440. doi: 10.1021/jacs.8b02982

    25. [25]

      Chen C T, Huang W P. A highly selective fluorescent chemosensor for lead ions[J]. J. Am. Chem. Soc., 2002,124:6246-6247. doi: 10.1021/ja025710e

    26. [26]

      Harnden A C, Suturina E A, Batsanov A S, Fox M A, Mason K, Vonci M, Mclnnes E J L, Chilton N F, Parker D. Unravelling the complexities of pseudocontact shift analysis in lanthanide coordination complexes of differing symmetry[J]. Angew. Chem. Int. Ed., 2019,58(30):10290-10294. doi: 10.1002/anie.201906031

    27. [27]

      Wang Z, Huang L Z, Zhu X F, Zhou X, Chi L F. An ultrasensitive organic semiconductor NO2 sensor based on crystalline TIPS-pentacene films[J]. Adv. Mater., 2017,29(38)1703192. doi: 10.1002/adma.201703192

    28. [28]

      Robert S, Marshall S, Ralph C, Elizabeth K. Identification and classification of carcinogens: Procedures of the Chemical Substances Threshold Limit Value Committee, ACGIH[J]. Am. J. Public Health, 1986,76:1232-1235. doi: 10.2105/AJPH.76.10.1232

    29. [29]

      Wang C, Wu E, Wu X D, Xu X C, Zhang G Q, Pu L. Enantioselective fluorescent recognition in the fluorous phase: Enhanced reactivity and expanded chiral recognition[J]. J. Am. Chem. Soc., 2015,137:3747-3750. doi: 10.1021/ja512569m

    30. [30]

      Latva M, Takalo H, Mukkala V M, Matachescu C, Rodriguez U, Kankare J. Correlation between the lowest triplet state energy level of the ligand and lanthanide (Ⅲ) luminescence quantum yield[J]. J. Lumin., 1997,75:149-169. doi: 10.1016/S0022-2313(97)00113-0

  • 加载中
    1. [1]

      Jun LUOBaoshu LIUYunchang ZHANGBingkai WANGBeibei GUOLan SHETianheng 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]

      Haitang WANGYanni LINGXiaqing MAYuxin CHENRui ZHANGKeyi WANGYing ZHANGWenmin WANG . Construction, crystal structures, and biological activities of two Ln3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188

    3. [3]

      Hao BAIWeizhi JIJinyan CHENHongji LIMingji 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

    4. [4]

      Tianyun Chen Ruilin Xiao Xinsheng Gu Yunyi Shao Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017

    5. [5]

      Liang TANGJingfei NIKang XIAOXiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139

    6. [6]

      Xingchao Zhao Xiaoming Li Ming Liu Zijin Zhao Kaixuan Yang Pengtian Liu Haolan Zhang Jintai Li Xiaoling Ma Qi Yao Yanming Sun Fujun Zhang . 倍增型全聚合物光电探测器及其在光电容积描记传感器上的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2311021-. doi: 10.3866/PKU.WHXB202311021

    7. [7]

      Jiarong Feng Yejie Duan Chu Chu Dezhen Xie Qiu'e Cao Peng Liu . Preparation and Application of a Streptomycin Molecularly Imprinted Electrochemical Sensor: A Suggested Comprehensive Analytical Chemical Experiment. University Chemistry, 2024, 39(8): 295-305. doi: 10.3866/PKU.DXHX202401016

    8. [8]

      Xiaowei TANGShiquan XIAOJingwen SUNYu ZHUXiaoting CHENHaiyan 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

    9. [9]

      Yang YANGPengcheng LIZhan SHUNengrong TUZonghua WANG . Plasmon-enhanced upconversion luminescence and application of molecular detection. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 877-884. doi: 10.11862/CJIC.20230440

    10. [10]

      Qilong Fang Yiqi Li Jiangyihui Sheng Quan Yuan Jie Tan . Magical Pesticide Residue Detection Test Strips: Aptamer-based Lateral Flow Test Strips for Organophosphorus Pesticide Detection. University Chemistry, 2024, 39(5): 80-89. doi: 10.3866/PKU.DXHX202310004

    11. [11]

      Jingjing QINGFan HEZhihui LIUShuaipeng HOUYa LIUYifan JIANGMengting TANLifang HEFuxing ZHANGXiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003

    12. [12]

      Jinghan ZHANGGuanying 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

    13. [13]

      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

    14. [14]

      Yongzhi LIHan ZHANGGangding WANGYanwei SUILei HOUYaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307

    15. [15]

      Yuanpei ZHANGJiahong WANGJinming HUANGZhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077

    16. [16]

      Qiaoqiao BAIAnqi ZHOUXiaowei LITang LIUSong LIU . Construction of pressure-temperature dual-functional flexible sensors and applications in biomedicine. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2259-2274. doi: 10.11862/CJIC.20240128

    17. [17]

      Cheng Zheng Shiying Zheng Yanping Zhang Shoutian Zheng Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131

    18. [18]

      Changqing MIAOFengjiao CHENWenyu LIShujie WEIYuqing YAOKeyi WANGNi WANGXiaoyan XINMing FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192

    19. [19]

      Shengbiao Zheng Liang Li Nini Zhang Ruimin Bao Ruizhang Hu Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096

    20. [20]

      Tongyu Zheng Teng Li Xiaoyu Han Yupei Chai Kexin Zhao Quan Liu Xiaohui Ji . A DIY pH Detection Agent Using Persimmon Extract for Acid-Base Discoloration Popularization Experiment. University Chemistry, 2024, 39(5): 27-36. doi: 10.3866/PKU.DXHX202309107

Metrics
  • PDF Downloads(3)
  • Abstract views(1163)
  • HTML views(176)

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