A Heterocyclic Aromatic Halide Small Molecule Fluorescent Probe for the Detection of 2,4,6-Trinitrophenol

doi:10.11944/j.issn.1000-0518.2020.03.190286

Chinese Journal of Applied Chemistry ›› 2020, Vol. 37 ›› Issue (3): 332-339.DOI: 10.11944/j.issn.1000-0518.2020.03.190286

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A Heterocyclic Aromatic Halide Small Molecule Fluorescent Probe for the Detection of 2,4,6-Trinitrophenol

DONG Ziyue,ZHOU Xiaoxia,ZHAO Xiaohui,YE Daying,AN Yue()

College of Chemistry and Chemical Engineering, Liaoning Normal University,Dalian,Liaoning 116029,China

Received:2019-10-25 Accepted:2020-01-03 Published:2020-03-01 Online:2020-03-10
Contact: AN Yue
Supported by:
Supported by the Natural Fund of Science and Technology Department of Liaoning Province(No.2019-ZD-0470)

Abstract

Abstract:

The heterocyclic aromatic halide, 2-chloro-5-(3-chloro-2,6-dimethoxyphenyl)-1,3,4-thiadiazole (L), was synthesized by Gattermann reaction from the aminothiadiazole derivative. Its structure was characterized by nuclear magnetic resonance spectroscopy (NMR) and high resolution mass spectrometry (HRMS). Probe L was used as a small molecule fluorescent probe to detect 2,4,6-trinitrophenol (TNP), and its fluorescence characteristics were systematically studied. Furthermore, combined with theoretical calculations, the possible quenching mechanism was explored. The results showed that the probe L had high seletivity, high sensitivity and strong anti-interference ability to TNP, and exhibited good fluorescence performance in a wide pH range. It has lower detection limit (4.2×10^-7 mol/L) and can be used for the detection of TNP in actual water samples.

Key words: heterocyclic aromatic halide, fluorescent probe, 2,4,6-trinitrophenol, theoretical calculations

DONG Ziyue, ZHOU Xiaoxia, ZHAO Xiaohui, YE Daying, AN Yue. A Heterocyclic Aromatic Halide Small Molecule Fluorescent Probe for the Detection of 2,4,6-Trinitrophenol[J]. Chinese Journal of Applied Chemistry, 2020, 37(3): 332-339.

References

[1]	SUN Wanfu,GUO Xiuyun,LI Yuncai.Hazardous Chemical Safety Technology Book. 3nd ed[M]. Beijing:Chemical Industry Press,2018:1316-1318(in Chinese). 孙万付,郭秀云,李运才. 危险化学品安全技术全书第三版[M]. 北京:化学工业出版社,2018:1316-1318.
[2]	Ma Y H,Zhao L,Li Y,et al. Investigation on Sensing Mechanism of a Fluorescent Probe for TNP Detection in Aqueous Solution[J]. Tetrahedron,2018,74(21):2684-2691.
[3]	Ding H L,Chen L D,Wang N,et al. Two Highly Selective and Sensitive Fluorescent Imidazole Derivatives Design and Application for 2,4,6-Trinitrophenol Detection[J]. Talanta,2019,195:345-353.
[4]	Chen L D,Ding H L,Wang N,et al. Two Highly Selective and Sensitive Fluorescent Probes Design and Apply to Specific Detection of Hypochlorite[J]. Dyes Pigm,2019,161:510-518.
[5]	YANG Hongbao,DU Jianjun,ZOU Li,et al. Specific Colorimetric Probe for Cu(Ⅱ) in Aqueous Solution and Its Application in Indicator Paper[J]. CIESC J,2014,66(2):592-596(in Chinese). 杨洪宝,杜健军,邹立,等. 染料探针分子对水中铜离子的可视化识别及试纸化应用[J]. 化工学报,2014,66(2):592-596.
[6]	HU Mingming,FAN Jiangli,LI Honglin,et al. A Sentive Probe for Determination of Cu2+ with Optical Detection in Aqueous Solution[J]. Chinese J Anal Chem,2011,39(8):1195-1200(in Chinese). 胡明明,樊江莉,李宏林,等. 荧光探针可视化检测水溶液中铜离子[J]. 分析化学,2011,39(8):1195-1200.
[7]	Zhu H,Fan J L,Du J J,et al. Fluorescent Probes for Sensing and Imaging within Specific Cellular Organelles[J]. Acc Chem Res,2016,49(10):2115-2126.
[8]	Jiang N,Fan J L,Xu F,et al. Ratiometric Fluorescence Imaging of Cellular Polarity: Decrease in Mitochondrial Polarity in Cancer Cells[J]. Angew Chem,2015,127(8):2540-2544.
[9]	Hussain S,Malik A K,Afroz M A,et al. Ultrasensitive Detection of Nitroexplosive-Picric Acid via a Conjugated Polyelectrolyte in Aqueous Media and Solid Support[J]. Chem Commun,2015,51(33):7207-7210.
[10]	Liu T H,Ding L P,He G,et al. Photochemical Stabilization of Terthiophene and Its Utilization as a New Sensing Element in the Fabrication of Monolayer-Chemistry-Based Fluorescent Sensing Films[J]. ACS Appl Mater Interfaces,2011,3(4):1245-1253.
[11]	Ding L P,Bai Y M,Cao Y,et al. Micelle-Induced Versatile Sensing Behavior of Bispyrene-Based Fluorescent Molecular Sensor for Picric Acid and PYX Explosives[J]. Langmuir,2014,30(26):7645-7653.
[12]	Hu Z C,Deibert B J,Li J.ChemInform Abstract:Luminescent Metal-Organic Frameworks for Chemical Sensing and Explosive Detection[J]. Chem Soc Rev,2014,43(16):5815-5840.
[13]	Qin A J,Tang L,Lam J W Y,et al. Metal-Free Click Polymerization:Synthesis and Photonic Properties of Poly(aroyltriazole)s[J]. Adv Funct Mater,2009,19(12):1891-1900.
[14]	Hu R R,Maldonado J L,Rodriguez M,et al. Luminogenic Materials Constructed from Tetraphenylethene Building Blocks:Synthesis, Aggregation-Induced Emission, Two-Photon Absorption, Light Refraction, and Explosive Detection[J]. J Mater Chem,2011,22(1):232-240.
[15]	Li D D,Liu J Z,Kwok R T K,et al. Supersensitive Detection of Explosives by Recyclable AIE Luminogen-Functionalized Mesoporous Materials[J]. Chem Commun,2012,48(57):7167-7169.
[16]	REN Yifei,HAO Hongxia,YANG Ruiqin.Recent Progress in Research of Fluorescent Probes for Detection of 2,4,6-Trinitrophenol[J]. Forensic Sci Technol,2018,43(2):104-110(in Chinese). 任翼飞,郝红霞,杨瑞琴. 荧光探针检测2,4,6-三硝基苯酚研究进展[J]. 刑事技术,2018,43(2):104-110.
[17]	Pandith A,Kumar A,Lee J Y,et al. 9-Anthracenecarboxamide Fluorescent Probes for Selective Discrimination of Picric Acid from Mono- and Di-nitrophenols in Ethanol[J]. Tetrahedron Lett,2015,56(51):7094-7099.
[18]	Ma Y H,Zhao L,Li Y,et al. Investigation on Sensing Mechanism of a Fluorescent Probe for TNP Detection in Aqueous Solution[J]. Tetrahedron,2018,74(21):2684-2691.
[19]	Long Y Y,Chen H B,Wang H M,et al. Highly Sensitive Detection of Nitroaromatic Explosives Using an Electrospun Nanofibrous Sensor Based on a Novel Fluorescent Conjugated Polymer[J]. Anal Chim Acta,2012,744:82-91.
[20]	Li J,Wang N,Liu W T,et al. A Revisit to Gattermann Reaction: Interesting Synthesis of Nitrogen Heterocyclic Aromatic Halides and Their Fluorescence Properties[J]. New J Chem,2017,41(20):12225.
[21]	Linciano P,Dawson A,Pohner I,et al. Exploiting the 2-Amino-1,3,4-thiadiazole Scaffold to Inhibit Trypanosoma brucei Pteridine Reductase in Support of Early-Stage Drug Discovery[J]. ACS Omega,2017,2(9):5666-5683.
[22]	Yan J,Ni J C,Zhao J X,et al. The Nitro Aromatic Compounds Detection by Triazole Carboxylic Acid and Its Complex with the Fluorescent Property[J]. Tetrahedron,2017,73(18):2682-2689.
[23]	WEI Yongju,LI Na,QIN Shenjun.Fluorescence Spectra and Fluorescence Quantum Yield of Sulfosalicylic Acid[J]. Spectrosc Spectr Anal,2004,24(6):647-651(in Chinese). 魏永巨,李娜,秦身钧. 磺基水杨酸的荧光光谱与荧光量子产率[J]. 光谱学与光谱分析,2004,24(6):647-651.

A Heterocyclic Aromatic Halide Small Molecule Fluorescent Probe for the Detection of 2,4,6-Trinitrophenol

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