Citation: Yan Ni, Song Jiale, Wang Fengyan, Kan Longwang, Song Jiahang, Wang Weiling, Ma Wenqiang, Zhang Weidong, He Gang. Pyrenoviologen-based fluorescent sensor for detection of picric acid in aqueous solution[J]. Chinese Chemical Letters, ;2019, 30(11): 1984-1988. doi: 10.1016/j.cclet.2019.09.039 shu

Pyrenoviologen-based fluorescent sensor for detection of picric acid in aqueous solution

Yan Ni ^a,*, ,
Song Jiale ^a ,
Wang Fengyan ^a ,
Kan Longwang ^a ,
Song Jiahang ^a ,
Wang Weiling ^a ,
Ma Wenqiang ^b ,
Zhang Weidong ^b ,
He Gang ^b,*,

a.
Polymer Materials & Engineering Department, School of Materials Science & Engineering, Engineering Research Center of Transportation Materials, Ministry of Education, Chang'an University, Xi'an 710064, China
b.
Frontier Institute of Science and Technology, State Key Laboratory for Strength and Vibration of Mechanical Structures, Xi'an Jiaotong University, Xi'an 710054, China

niyan@chd.edu.cn

ganghe@mail.xjtu.edu.cn

Received Date: 8 August 2019
Revised Date: 18 September 2019
Accepted Date: 19 September 2019
Available Online: 19 November 2019

Figures(8)

Two highly emissive pyrenoviologen derivatives were synthesized and used to fabricate fluorescent sensors for detection of picric acid (PA) with good sensitivity and selectivity. The sensitivity of the sensor was attributed to the specific electrostatic association effect of the cationic pyrenoviologens to the picrate anions, which also gave the sensor special selectivity among other compounds with similar structure. The electron transfer between them was attributed to the fluorescence response. Fluorescence lifetime measurements revealed that the quenching is static in nature. The novel and efficient pyrenoviologen derivatives-based sensors offered a strategy to fabricate real-life PA sensor.
- Viologen,
- Explosives,
- Picric acid,
- Pyrene,
- Fluorescent sensor
1. [1]
  G.V. Perez, A.L. Perez, J. Chem. Educ. 77 (2000) 910.
2. [2]
  B. Roy, A.K. Bar, B. Gole, P.S. Mukherjee, J. Org. Chem. 78 (2013) 1306-1310. doi: 10.1021/jo302585a
3. [3]
  H. Sohn, R.M. Calhoun, M.J. Sailor, W.C. Trogler, Angew. Chem. Int. Ed. 40 (2001) 2104-2105. doi: 10.1002/1521-3773(20010601)40:11<2104::AID-ANIE2104>3.0.CO;2-%23
4. [4]
  T. Feng, X. Li, J. Wu, C. He, C. Duan, Chin. Chem. Lett. (2019), doi: http://dx.doi.org/10.1016/j.cclet.2019.04.059.
5. [5]
  M. Cameron, Picric Acid Hazards, American Industrial Hygiene Association, Fairfax, VA, 1995.
6. [6]
  M. Nipper, Y. Qian, R. Scott Carr, K. Miller, Chemosphere 56 (2004) 519-530. doi: 10.1016/j.chemosphere.2004.04.039
7. [7]
  M.E. Germain, M.J. Knapp, Chem. Soc. Rev. 38 (2009) 2543-2555. doi: 10.1039/b809631g
8. [8]
  X. Sun, Y. Wang, Y. Lei, Chem. Soc. Rev. 44 (2015) 8019-8061. doi: 10.1039/C5CS00496A
9. [9]
  S. Rochat, T.M. Swager, ACS Appl. Mater. Interfaces 5 (2013) 4488-4502. doi: 10.1021/am400939w
10. [10]
  U.H.F. Bunz, K. Seehafer, M. Bender, M. Porz, Chem. Soc. Rev. 44 (2015) 4322-4336. doi: 10.1039/C4CS00267A
11. [11]
  W.M. Wan, D. Tian, Y.N. Jing, et al., Angew. Chem. Int. Ed. 57 (2018) 15510-15516. doi: 10.1002/anie.201809844
12. [12]
  W. Zhang, D. Yu, Z. Wang, et al., Org. Lett. 21 (2019) 109-113. doi: 10.1021/acs.orglett.8b03538
13. [13]
  W. Zhang, G. Li, L. Xu, et al., Chem. Sci. 9 (2018) 4444-4450. doi: 10.1039/C8SC00688A
14. [14]
  K.M. Hindi, M.J. Panzner, C.A. Tessier, C.L. Cannon, W.J. Youngs, Chem. Rev.109 (2009) 3859-3884. doi: 10.1021/cr800500u
15. [15]
  L. Ding, Y. Fang, Chem. Soc. Rev. 39 (2010) 4258-4273. doi: 10.1039/c003028g
16. [16]
  S.S. Nagarkar, A.V. Desai, S.K. Ghosh, CrystEngComm 18 (2016) 2994-3007. doi: 10.1039/C6CE00244G
17. [17]
  A. Beneduci, S. Cospito, M. La Deda, G. Chidichimo, Adv. Funct. Mater. 25 (2015) 1240-1247. doi: 10.1002/adfm.201403611
18. [18]
  X. Wang, N. Gan, M. Gu, et al., Chin. Chem. Lett. (2018), doi: http://dx.doi.org/10.1016/j.cclet.2018.12.023.
19. [19]
  A. Chowdhury, P.S. Mukherjee, J. Org. Chem. 80 (2015) 4064-4075. doi: 10.1021/acs.joc.5b00348
20. [20]
  G. He, H. Peng, T. Liu, et al., J. Mater. Chem. 19 (2009) 7347-7353. doi: 10.1039/b906946a
21. [21]
  L. Striepe, T. Baumgartner, Chem. -Eur. J. 23 (2017) 16924-16940. doi: 10.1002/chem.201703348
22. [22]
  S.L. Li, M. Han, Y. Zhang, et al., J. Am. Chem. Soc. 141 (2019) 12663-12672. doi: 10.1021/jacs.9b04930
23. [23]
  K. Murugavel, Polym. Chem. 5 (2014) 5873-5884. doi: 10.1039/C4PY00718B
24. [24]
  H. Chen, H. Yang, W.C. Xu, Y.B. Tan, Chin. Chem. Lett. 24 (2013) 857-860. doi: 10.1016/j.cclet.2013.05.028
25. [25]
  T.T. Cao, X.Y. Yao, J. Zhang, Q.C. Wang, X. Ma, Chin. Chem. Lett. 26 (2015) 867-871. doi: 10.1016/j.cclet.2015.01.032
26. [26]
  G. Li, L. Xu, W. Zhang, et al., Angew. Chem. Int. Ed. 57 (2018) 4897-4901. doi: 10.1002/anie.201711761
27. [27]
  G. Li, B. Zhang, J. Wang, et al., Angew. Chem. Int. Ed. 58 (2019) 8468-8473. doi: 10.1002/anie.201903152
28. [28]
  A.N. Woodward, J.M. Kolesar, S.R. Hall, et al., J. Am. Chem. Soc.139 (2017) 8467-8473. doi: 10.1021/jacs.7b01005
29. [29]
  Z. Wang, W. Bai, J. Tong, et al., Chem. Commun. 52 (2016) 10365-10368. doi: 10.1039/C6CC02851A
30. [30]
  X. Zhang, E.L. Clennan, N. Arulsamy, R. Weber, J. Weber, J. Org. Chem. 81 (2016) 5474-5486. doi: 10.1021/acs.joc.6b00835
31. [31]
  N. Yan, Z. Xu, K.K. Diehn, et al., J. Am. Chem. Soc. 135 (2013) 8989-8999. doi: 10.1021/ja402560n
32. [32]
  N. Yan, Z. Xu, K.K. Diehn, et al., Langmuir 29 (2013) 793-805. doi: 10.1021/la304957n
33. [33]
  Q. Hu, C. Qin, L. Huang, et al., Dyes Pigment. 149 (2018) 253-260. doi: 10.1016/j.dyepig.2017.10.002
34. [34]
  S. Zhang, F. Lü, L. Gao, L. Ding, Y. Fang, Langmuir 23 (2007) 1584-1590. doi: 10.1021/la062773s
35. [35]
  G. He, N. Yan, J. Yang, et al., Macromolecules 44 (2011) 4759-4766. doi: 10.1021/ma200953s
36. [36]
  M. Hariharan, J. Joseph, D. Ramaiah, J. Phys. Chem. B 110 (2006) 24678-24686. doi: 10.1021/jp063079o
37. [37]
  M. Hariharan, S.C. Karunakaran, D. Ramaiah, I. Schulz, B. Epe, Chem. Commun. 46 (2010) 2064-2066. doi: 10.1039/b924943e
38. [38]
  S. Hagiwara, Y. Ishida, D. Masui, T. Shimada, S. Takagi, Tetrahedron Lett. 53 (2012) 5800-5802. doi: 10.1016/j.tetlet.2012.08.079
39. [39]
  D. Morimoto, K. Sato, K. Saito, et al., J. Photochem. Photobiol. A 337 (2017) 112-117. doi: 10.1016/j.jphotochem.2017.01.023
40. [40]
  K. Sato, S. Hagiwara, D. Morimoto, et al., J. Photochem. Photobiol. A 313 (2015) 9-14. doi: 10.1016/j.jphotochem.2015.05.015
41. [41]
  D. Morimoto, H. Yoshida, K. Sato, et al., Langmuir 33 (2017) 3680-3684. doi: 10.1021/acs.langmuir.7b00512
42. [42]
  N. Sun, K. Su, Z. Zhou, et al., ACS Appl. Mater. Interfaces 10 (2018) 16105-16112. doi: 10.1021/acsami.8b01624
43. [43]
  Z. Wang, W. Bai, J. Tong, et al., Chem. Commun. 52 (2016) 10365-10368. doi: 10.1039/C6CC02851A
44. [44]
  Y. Cheng, J. Wang, Z. Qiu, et al., Adv. Mater. 29 (2017)1703900.
45. [45]
  C. Duan, M. Won, P. Verwilst, et al., Anal. Chem. 91 (2019) 4172-4178. doi: 10.1021/acs.analchem.9b00224
46. [46]
  J. Wu, L. Jiang, P. Verwilst, et al., Chem. Commun. 55 (2019) 9947-9950. doi: 10.1039/C9CC05048E
47. [47]
  Y. Xu, B. Li, W. Li, et al., Chem. Commun. 49 (2013) 4764-4766. doi: 10.1039/c3cc41994k
48. [48]
  Y. Su, W. Shi, X. Chen, et al., RSC Adv. 6 (2016) 41340-41347. doi: 10.1039/C6RA06942H
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