Citation: Hong-Xing Zhang, Ren-Bo Wei, Chuan-Zhi Chen, Xin-Lin Tuo, Xiao-Gong Wang. A novel fluorescent epoxy resin for organophosphate pesticide detection[J]. Chinese Chemical Letters, ;2015, 26(1): 39-42. doi: 10.1016/j.cclet.2014.10.014 shu

A novel fluorescent epoxy resin for organophosphate pesticide detection

1.
a Department of Chemical Engineering, Laboratory of Advanced Materials (MOE), Tsinghua University, Beijing 100084, China;
2.
b Department of Chemical Defense, Institute of Chemical Defense, Beijing 102205, China

Corresponding author: Xiao-Gong Wang,
Received Date: 18 August 2014
Available Online: 29 September 2014
Fund Project: Financial supports from the Research Foundation of the General Armament Department (No. 2008 CD 012) are gratefully acknowledged. (No. 2008 CD 012)

In this work, a novel bisbenzimidazolylpyridine-functionalized fluorescent epoxy resin was synthesized for organophosphate pesticide detection. The epoxy resin was characterized by Fourier-transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance spectroscopy (¹H NMR), gel permeation chromatography (GPC), differential scanning calorimetry (DSC) and fluorescence spectroscopy. After loading with Eu(Ⅲ) ions, the epoxy resin showed a strong fluorescence emission. The fluorescence emission was observed to be instantaneously quenched when exposed to trace amount of diethyl chlorophosphate in solution. The Stern-Volmer quenching constants K_sv for quenching at 617 nm was determined to be 0.377×10³ L/mol. This sensitive emission-quenching function and easy processing nature of the polymeric support enable the resin to be a promising chemosensor candidate for the detection of organophosphates.
- MeBIP,
- Epoxy resin,
- Europium complex,
- Fluorescence quenching,
- Organophosphates
1. [1]
  [1] F. Ariese, W.H.O. Ernst, D.T.H.M. Sijm, Natural and synthetic organic compounds in the environment - a symposium report, Environ. Toxicol. Pharmacol. 10 (2001) 65-80.
2. [2]
  [2] C.H. Gunderson, C.R. Lehmann, F.R. Sidell, B. Jabbari, Nerve agents: a review, Neurology 42 (1992) 946-950.
3. [3]
  [3] S. Bencic-Nagale, T. Sternfeld, D.R. Walt, Microbead chemical switches: an approach to detection of reactive organophosphate chemical warfare agent vapors, J. Am. Chem. Soc. 128 (2006) 5041-5048.
4. [4]
  [4] A. Barba-Bon, A.M. Costero, S. Gil, A. Harriman, F. Sancenón, Highly selective detection of nerve-agent simulants with BODIPY dyes, Chem. Eur. J. 20 (2014) 1-10.
5. [5]
  [5] R. Subramaniam, C. Astot, L. Juhlin, C. Nilsson, A. Ostin, Direct derivatization and rapid GC-MS screening of nerve agent markers in aqueous samples, Anal. Chem. 82 (2010) 7452-7459.
6. [6]
  [6] M.S. Nieuwenhuizen, J.L.N. Harteveld, Studies on a surface acoustic wave (SAW) dosimeter sensor for organophosphorous nerve agents, Sens. Actuators B 40 (1997) 167-173.
7. [7]
  [7] Q.Q. Li, Y.P. Du, Y. Xu, et al., Rapid and sensitive detection of pesticides by surfaceenhanced Raman spectroscopy technique based on glycidyl methacrylate-ethylene dimethacrylate (GMA-EDMA) porous material, Chin. Chem. Lett. 24 (2013) 332-334.
8. [8]
  [8] O.S. Wolfbeis, Fiber-optic chemical sensors and biosensors, Anal. Chem. 76 (2004) 3269-3284.
9. [9]
  [9] K. Chulvi, P. Gaviña, A.M. Costero, et al., Discrimination of nerve gases mimics and other organophosphorous derivatives in gas phase using a colorimetric probe array, Chem. Commun. 48 (2012) 10105-10107.
10. [10]
  [10] J. Lee, S. Seo, J. Kim, Colorimetric detection of warfare gases by polydiacetylenes toward equipment-free detection, Adv. Funct. Mater. 22 (2012) 1632-1638.
11. [11]
  [11] S. Royo, R. Martínez-Máñez, F. Sancenón, et al., Chromogenic and fluorogenic reagents for chemical warfare nerve agents' detection, Chem. Commun. 46 (2007) 4839-4847.
12. [12]
  [12] I. Walton, M. Davis, L. Munro, et al., A fluorescent dipyrrinone oxime for the detection of pesticides and other organophosphates, Org. Lett. 14 (2012) 2686-2689.
13. [13]
  [13] S.W. Zhang, T.M. Swager, Fluorescent detection of chemical warfare agents: functional group specific ratiometric chemosensors, J. Am. Chem. Soc. 125 (2003) 3420-3421.
14. [14]
  [14] D. Knapton, M. Burnworth, S.J. Rowan, C. Weder, Fluorescent organometallic sensors for the detection of chemical-warfare-agent mimics, Angew. Chem. Int. Ed. 45 (2006) 5825-5829.
15. [15]
  [15] T.J. Dale, J.J. Rebek, Fluorescent sensors for organophosphorus nerve agent mimics, J. Am. Chem. Soc. 128 (2006) 4500-4501.
16. [16]
  [16] Y.C. Bai, C. Zhang, C.H. Xu, C.H. Yan, Fluorescent molecular probes for the detection of chemical warfare agents and their mimics, Front. Chem. Chin. 5 (2010) 123-133.
17. [17]
  [17] M. Burnworth, S.J. Rowan, C. Weder, Fluorescent sensors for the detection of chemical warfare agents, Chem. Eur. J. 13 (2007) 7828-7836.
18. [18]
  [18] H.X. Zhang, X.F. Hua, X.L. Tuo, X.G. Wang, Synthesis and fluorescent properties of a novel europium(Ⅲ) complex with terpyridine-capped poly(ethylene glycol), J. Rare Earths 30 (2012) 705-708.
19. [19]
  [19] S. Sarkar, A. Mondal, A.K. Tiwari, R. Shunmugam, Unique emission from norbornene derived terpyridine-a selective chemodosimeter for G-type nerve agent surrogates, Chem. Commun. 48 (2012) 4223-4225.
20. [20]
  [20] H.X. Zhang, X.F. Hua, X.L. Tuo, et al., Polymer microsphere-based lanthanide luminescent chemosensor for detection of organophosphate pesticides, J. Rare Earths 30 (2012) 1203-1207.
21. [21]
  [21] R. Shunmugam, G.N. Tew, Terpyridine-lanthanide complexes respond to fluorophosphate containing nerve gas G-agent surrogates, Chem. Eur. J. 14 (2008) 5409-5412.
22. [22]
  [22] J.B. Beck, S.J. Rowan, Metal-ligand induced supramolecular polymerization: a route to responsive materials, Faraday Dis. 128 (2005) 43-53.
23. [23]
  [23] X.G. Wang, K. Yang, J. Kumar, et al., Heteroaromatic chromophore functionalized epoxy-based nonlinear optical polymers, Macromolecules 31 (1998) 4126-4134.
1. [1]
  Zhaoru Chen , Xiaoxu Liu , Haonan Chen , Jialong Li , Xiaofeng Wang , Jianfeng Zhu . Application of epoxy resin in cultural relics protection. Chinese Chemical Letters, 2024, 35(4): 109194-. doi: 10.1016/j.cclet.2023.109194
2. [2]
  Junqing Wu , Yiyang Zhang , Qingqing Hong , Hui Yang , Lifeng Zhang , Ming Zhang , Lei Yu . Organometallic modification of silica with europium endowing the fluorescence properties: The key technique for numerical quality monitoring. Chinese Chemical Letters, 2025, 36(4): 110165-. doi: 10.1016/j.cclet.2024.110165
3. [3]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
4. [4]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
5. [5]
  Chunhui Zhang , Jie Wang , Jieyang Zhan , Runmin Yang , Guanggang Gao , Jiayuan Zhang , Linlin Fan , Mengqi Wang , Hong Liu . Highly sensitive hydrazine detection through a novel Raman scattering quenching mechanism enabled by a crystalline and noble metal–free polyoxometalate substrate. Chinese Chemical Letters, 2025, 36(3): 109719-. doi: 10.1016/j.cclet.2024.109719
6. [6]
  Junchen Peng , Xue Yin , Dandan Dong , Zhongyuan Guo , Qinqin Wang , Minmin Liu , Fei He , Bin Dai , Chaofeng Huang . Promotion effect of epoxy group neighboring single-atom Cu site on acetylene hydrochlorination. Chinese Chemical Letters, 2024, 35(6): 109508-. doi: 10.1016/j.cclet.2024.109508
7. [7]
  Dongmei Yao , Junsheng Zheng , Liming Jin , Xiaomin Meng , Zize Zhan , Runlin Fan , Cong Feng , Pingwen Ming . Effect of surface oxidation on the interfacial and mechanical properties in graphite/epoxy composites composite bipolar plates. Chinese Chemical Letters, 2024, 35(11): 109382-. doi: 10.1016/j.cclet.2023.109382
8. [8]
  Chao Ma , Cong Lin , Jian Li . MicroED as a powerful technique for the structure determination of complex porous materials. Chinese Journal of Structural Chemistry, 2024, 43(3): 100209-100209. doi: 10.1016/j.cjsc.2023.100209
9. [9]
  Mengjuan Sun , Muye Zhou , Yifang Xiao , Hailei Tang , Jinhua Chen , Ruitao Zhang , Chunjiayu Li , Qi Ya , Qian Chen , Jiasheng Tu , Qiyue Wang , Chunmeng Sun . Reversibly size-switchable polyion complex micelles for antiangiogenic cancer therapy. Chinese Chemical Letters, 2024, 35(7): 109110-. doi: 10.1016/j.cclet.2023.109110
10. [10]
  Yuanjin Chen , Xianghui Shi , Dajiang Huang , Junnian Wei , Zhenfeng Xi . Synthesis and reactivity of cobalt dinitrogen complex supported by nonsymmetrical pincer ligand. Chinese Chemical Letters, 2024, 35(7): 109292-. doi: 10.1016/j.cclet.2023.109292
11. [11]
  Peng Meng , Qian-Cheng Luo , Aidan Brock , Xiaodong Wang , Mahboobeh Shahbazi , Aaron Micallef , John McMurtrie , Dongchen Qi , Yan-Zhen Zheng , Jingsan Xu . Molar ratio induced crystal transformation from coordination complex to coordination polymers. Chinese Chemical Letters, 2024, 35(4): 108542-. doi: 10.1016/j.cclet.2023.108542
12. [12]
  Jingwen Zhao , Jianpu Tang , Zhen Cui , Limin Liu , Dayong Yang , Chi Yao . A DNA micro-complex containing polyaptamer for exosome separation and wound healing. Chinese Chemical Letters, 2024, 35(9): 109303-. doi: 10.1016/j.cclet.2023.109303
13. [13]
  Ya-Ping Liu , Zhi-Rong Gui , Zhen-Wen Zhang , Sai-Kang Wang , Wei Lang , Yanzhu Liu , Qian-Yong Cao . A phenylphenthiazide anchored Tb(Ⅲ)-cyclen complex for fluorescent turn-on sensing of ClO⁻. Chinese Chemical Letters, 2025, 36(2): 109769-. doi: 10.1016/j.cclet.2024.109769
14. [14]
  Minghui Zhang , Na Zhang , Qian Zhao , Chao Wang , Alexander Steiner , Jianliang Xiao , Weijun Tang . Cobalt pincer complex-catalyzed highly enantioselective hydrogenation of quinoxalines. Chinese Chemical Letters, 2025, 36(4): 110081-. doi: 10.1016/j.cclet.2024.110081
15. [15]
  Deshuai Zhen , Chunlin Liu , Qiuhui Deng , Shaoqi Zhang , Ningman Yuan , Le Li , Yu Liu . A review of covalent organic frameworks for metal ion fluorescence sensing. Chinese Chemical Letters, 2024, 35(8): 109249-. doi: 10.1016/j.cclet.2023.109249
16. [16]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
17. [17]
  Ying Xu , Chengying Shen , Hailong Yuan , Wei Wu . Mapping multiple phases in curcumin binary solid dispersions by fluorescence contrasting. Chinese Chemical Letters, 2024, 35(9): 109324-. doi: 10.1016/j.cclet.2023.109324
18. [18]
  Yuxin Li , Chengbin Liu , Qiuju Li , Shun Mao . Fluorescence analysis of antibiotics and antibiotic-resistance genes in the environment: A mini review. Chinese Chemical Letters, 2024, 35(10): 109541-. doi: 10.1016/j.cclet.2024.109541
19. [19]
  Ziyou Zhang , Te Ji , Hongliang Dong , Zhiqiang Chen , Zhi Su . Effect of coordination restriction on pressure-induced fluorescence evolution. Chinese Chemical Letters, 2024, 35(12): 109542-. doi: 10.1016/j.cclet.2024.109542
20. [20]
  Yingying Yan , Wanhe Jia , Rui Cai , Chun Liu . An AIPE-active fluorinated cationic Pt(Ⅱ) complex for efficient detection of picric acid in aqueous media. Chinese Chemical Letters, 2024, 35(5): 108819-. doi: 10.1016/j.cclet.2023.108819

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(648)
HTML views(1)

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