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

1.
Baotou Research Institute of Rare Earths, State Key Laboratory of Baiyunobo Rare Earth Resource Researches and Comprehensive Utilization, Baotou, Inner Mongolia 014030, China
2.
Key Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, China

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.
- lanthanide complex,
- luminous sensor,
- organic small-molecule amines,
- detection
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
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