Citation: Zhu Benzhan, Shao Bo, Mao Li, Gao Huiying. Intrinsic Chemiluminescence Production during Environmentally-friendly Advanced Oxidation of Halogenated Aromatics and Its Applications[J]. Acta Chimica Sinica, ;2016, 74(7): 557-564. doi: 10.6023/A16040178 shu

Intrinsic Chemiluminescence Production during Environmentally-friendly Advanced Oxidation of Halogenated Aromatics and Its Applications

1.
State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China

Corresponding author: Zhu Benzhan, bzhu@rcees.ac.cn
Received Date: 11 April 2016
Revised Date: 23 May 2016

Fund Project: National Natural Science Foundation of China 21577149Strategic Priority Research Program of CAS XDB01020300National Natural Science Foundation of China 21321004Open Foundation from State Key Laboratory of Environmental Chemistry and Ecotoxicology KF2012-09National Natural Science Foundation of China 21477139National Natural Science Foundation of China 21237005

Figures(7)

Haloaromatics (XAr) have been widely used as pesticides, personal care agents, pharmaceuticals and flame retardants, which are now ubiquitously present in our environment. The carcinogenicity coupled with their ubiquitous occurrence have raised public concerns on the potential risks to both human health and the ecosystem posed by XAr. Advanced oxidation processes (AOPs) have been increasingly employed as an "environmentally-friendly" technology for remediating such highly toxic and recalcitrant XAr. During these AOPs systems, the most reactive radical intermediate formed at near-ambient temperature and pressure is the hydroxyl radical (^·OH). Recently, we found that an intrinsic chemiluminescence can be generated during the advanced oxidation of the priority pollutant pentachlorophenol and all other XAr. Furtherly, by the complementary application of electron spin resonance (ESR) with 5, 5-dimethyl-1-pyrroline-N-oxide (DMPO) as the spin-trapping agent, fluorescence method with terephthalic acid (TPA) as the ^·OH probe, chemiluminescence analysis in the presence of classic ^·OH scavengers and several typical ^·OH-generating systems, the chemiluminescence was confirmed to be directly dependent on the production of the extremely reactive ^·OH. Further studies showed that halogenated quinoid intermediates were produced during the degradation of XAr by ^·OH-generating system, which could produce weak chemiluminescence that was greatly enhanced by addition of extra ^·OH. We proposed that this unusual chemiluminescence generation was due to hydroxyl radical-dependent production of halogenated quinoid intermediates and electronically excited carbonyl species. In addition, the time course of chemiluminescence emission correlated well with the degradation of XAr: when the degradation level of XAr reached the maximum, no further chemiluminescence emission could be observed. Based on these findings, we developed a rapid, sensitive, simple, and effective chemiluminescence method to not only measure trace amount of XAr, but also monitor their real-time degradation kinetics. These new findings may have broad chemical, pharmaceutical, toxicological and environmental implications for future studies on remediation of these halogenated persistent organic pollutants by AOPs.
- chemiluminescence,
- halogenated aromatics,
- hydroxyl radicals,
- advanced oxidation processes,
- Fenton and Fenton-like reactions
1. [1]
  Zhu, B. Z.; Shan, G. Q. Chem. Res. Toxicol. 2009, 22, 969. doi: 10.1021/tx900030v
2. [2]
  Zhu, B. Z.; Zhu, J. G.; Fan, R. M.; Mao, L. Adv. Mol. Toxicol. 2011, 5, 1. doi: 10.1016/B978-0-444-53864-2.00001-3
3. [3]
  Zhu, B. Z. Chin. Sci. Bull. 2009, 54, 1673. doi: 10.1360/972009-142
4. [4]
  Dann, A. B.; Hontela, A. J. Appl. Toxicol. 2010, 31, 285.
5. [5]
  de Wit, C. A. Chemosphere 2002, 46, 583. doi: 10.1016/S0045-6535(01)00225-9
6. [6]
  Ramamoorthy, S. Chlorinated Organic Compounds in the Environment: Regulatory and Monitoring Assessment, CRC Press, Boca Raton, FL, 1997.
7. [7]
  Fang, X. W.; Schuchmann, H. P.; von Sonntag, C. J. Chem. Soc. Perkin. Trans. 2000, 2, 1391.
8. [8]
  Zimbron, J. A.; Reardon, K. F. Water. Res. 2009, 43, 1831. doi: 10.1016/j.watres.2009.01.024
9. [9]
  Lan, Q.; Li, F.; Liu, C.; Li, X. Z. Environ. Sci. Technol. 2008, 42, 7918. doi: 10.1021/es801220n
10. [10]
  Gupta, S. S.; Stadler, M.; Noser, C. A.; Ghosh, A.; Steinhoff, B.; Lenoir, D.; Horwitz, C. P.; Schramm, K. W.; Collins, T. J. Science 2002, 296, 326. doi: 10.1126/science.1069297
11. [11]
  Sorokin, A.; Seris, J. L.; Meunier, B. Science 1995, 268, 1163. doi: 10.1126/science.268.5214.1163
12. [12]
  Zhang, H.; Huang, C. H. Environ. Sci. Technol. 2003, 37, 2421. doi: 10.1021/es026190q
13. [13]
  Zhong, Y.; Liang, X.; Zhong, Y.; Zhu, J.; Zhu, S.; Yuan, P.; He, H.; Zhang, J. Water. Res. 2012, 46, 4633. doi: 10.1016/j.watres.2012.06.025
14. [14]
  Peller, J.; Wiest, O.; Kamat, P. V. Chem. Eur. J. 2003, 9, 5379. doi: 10.1002/chem.v9:21
15. [15]
  Von Sonntag, C. Water. Sci. Technol. 2008, 58, 1015. doi: 10.2166/wst.2008.467
16. [16]
  Wang, J. N.; Xu, L. J. Crit. Rev. Environ. Sci. Technol. 2012, 42, 251. doi: 10.1080/10643389.2010.507698
17. [17]
  Pera-Titus, M.; García-Molina, V.; Baños, M. A.; Giménez, J.; Esplugas, S. Appl. Catal. B: Environ. 2004, 47, 219. doi: 10.1016/j.apcatb.2003.09.010
18. [18]
  Schuster, G. B. Acc. Chem. Res. 1979, 12, 366. doi: 10.1021/ar50142a003
19. [19]
  Matsumoto, M. J. Photochem. Photobiol. C 2004, 5, 27. doi: 10.1016/j.jphotochemrev.2004.02.001
20. [20]
  Almeida de Oliveira, M.; Bartoloni, F. H.; Augusto, F. A.; Ciscato, L. F. M. L.; Bastos, E. L.; Badder, W. J. J. Org. Chem. 2012, 77, 10537. doi: 10.1021/jo301309v
21. [21]
  Widder, E. A. Science 2010, 328, 704. doi: 10.1126/science.1174269
22. [22]
  Adam, W.; Kazakov, D. V.; Kazakov, V. P. Chem. Rev. 2005, 105, 3371. doi: 10.1021/cr0300035
23. [23]
  Grayeski, M. L. Anal. Chem. 1987, 59, 1243A. doi: 10.1021/ac00148a723
24. [24]
  McCapra, F. Methods Enzymol. 2000, 305, 3. doi: 10.1016/S0076-6879(00)05475-6
25. [25]
  Zhou, W.; Cao, Y.; Sui, D.; Lu, C. Angew. Chem. Int. Ed. 2016, 55, 4236. doi: 10.1002/anie.201511868
26. [26]
  Wang, D. B.; Zhao, L. X.; Guo, L. H.; Zhang, H.; Wan, B.; Yang, Y. Acta Chim. Sinica 2015, 73, 388. doi: 10.6023/A15010036
27. [27]
  Li, Y.; Liu, W. N.; Zheng, X. W. Acta Chim. Sinica 2015, 73, 749. doi: 10.6023/A15010047
28. [28]
  Mao, L.; Liu, Y. X.; Huang, C. H.; Gao, H. Y.; Kalyanaraman, B.; Zhu, B. Z. Environ. Sci. Technol. 2015, 49, 7940. doi: 10.1021/acs.est.5b01227
29. [29]
  Wardman, P.; Candeias, L. P. Radiat. Res. 1996, 145, 523. doi: 10.2307/3579270
30. [30]
  Goldstein, S.; Meyerstein, D.; Czapski, G. Free Radic. Biol. Med. 1993, 15, 435. doi: 10.1016/0891-5849(93)90043-T
31. [31]
  Zhu, B. Z.; Zhao, H. T.; Kalyanaraman, B.; Liu, J.; Shan, G. Q.; Du, Y. G.; Frei, B. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 3698. doi: 10.1073/pnas.0605527104
32. [32]
  Zhu, B. Z.; Kalyanaraman, B.; Jiang, G. B. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 17575. doi: 10.1073/pnas.0704030104
33. [33]
  Zhu, B. Z.; Shan, G. Q.; Huang, C. H.; Kalyanaraman, B.; Mao, L.; Du, Y. G. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 11466. doi: 10.1073/pnas.0900065106
34. [34]
  Zhu, B. Z.; Mao, L.; Huang, C. H.; Qin, H.; Fan, R. M.; Kalyanaraman, B.; Zhu, J. G. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 16046. doi: 10.1073/pnas.1204479109
35. [35]
  Zhu, B. Z.; Ren, F. R.; Mao, L.; Gao, H. Y.; Liu, Q. L.; Liu, P. Chin. Sci. Bull. 2015, 60, 1855. doi: 10.1360/N972015-00286
36. [36]
  Brunmark, A.; Cadenas, E. Free Radic. Biol. Med. 1987, 3, 169. doi: 10.1016/0891-5849(87)90002-5
37. [37]
  Weavers, L. K.; Malmstadt, N.; Hoffmann, M. R. Environ. Sci. Technol. 2000, 34, 1280. doi: 10.1021/es980795y
38. [38]
  Fukushima, M.; Tatsumi, K. Environ. Sci. Technol. 2001, 35, 1771. doi: 10.1021/es001088j
39. [39]
  Zhao, Y.; Qin, F.; Boyd, J. M.; Anichina, J.; Li, X. F. Anal. Chem. 2010, 82, 4599. doi: 10.1021/ac100708u
40. [40]
  Chignell, C. F.; Han, S. K.; Mouithys-Mickalad, A.; Sik, R. H.; Stadler, K.; Kadiiska, M. B. Toxicol. Appl. Pharmacol. 2008, 230, 17.Kelly, B. C.; Ikonomou, M. G.; Blair, J. D.; Morin, A. E.; Gobas, F. A. P. C. Science 2007, 317, 236. doi: 10.1016/j.taap.2008.01.035
1. [1]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
2. [2]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
3. [3]
  Borong Yu , Huijiao Zhang , Xinyu Zhang , Xiaoying Li , Shuming Chen , Zhangang Han . The Blue Elf in the Dark: Gradient Science Popularization Experiments on Chemiluminescence. University Chemistry, 2024, 39(9): 295-303. doi: 10.12461/PKU.DXHX202403107
4. [4]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
5. [5]
  Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
6. [6]
  Daojuan Cheng , Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105
7. [7]
  .
  CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
  . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.
8. [8]
  Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
9. [9]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
10. [10]
  Yuan GAO , Yiming LIU , Chunhui WANG , Zhe HAN , Chaoyue FAN , Jie 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
11. [11]
  Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
12. [12]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
13. [13]
  Jiajia Li , Xiangyu Zhang , Zhihan Yuan , Zhengyang Qian , Jian Zhu . 3D Printing Based on Photo-Induced Reversible Addition-Fragmentation Chain Transfer Polymerization. University Chemistry, 2024, 39(5): 11-19. doi: 10.3866/PKU.DXHX202309073
14. [14]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
15. [15]
  Qian Shao , Jiajing Tan , Yongmei Chen , Jiyue Jing , Zhuo Wang . Exploration and Practice on the Management of Extracurricular Innovation Laboratories in Chemistry. University Chemistry, 2024, 39(4): 19-25. doi: 10.3866/PKU.DXHX202310119
16. [16]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
17. [17]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
18. [18]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang 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
19. [19]
  Chi Zhang , Ning Ding , Yuwei Pan , Lichun Fu , Ying Zhang . The degradation pathways of contaminants by reactive oxygen species generated in the Fenton/Fenton-like systems. Chinese Chemical Letters, 2024, 35(10): 109579-. doi: 10.1016/j.cclet.2024.109579
20. [20]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1325)
HTML views(80)

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