Citation: Zhao Feifei, Wu Hongwei, Liu Chuanxiang, Mao Haifang. A Selective Colorimetric and Fluorescent Diphenylacetylene-Based Naphthalimide for Sensing of Cyanide[J]. Chinese Journal of Organic Chemistry, ;2016, 36(11): 2689-2694. doi: 10.6023/cjoc201605027 shu

A Selective Colorimetric and Fluorescent Diphenylacetylene-Based Naphthalimide for Sensing of Cyanide

1.
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418

Corresponding author: Liu Chuanxiang, cxliu@sit.edu.cn Mao Haifang, mhf@sit.edu.cn
Received Date: 16 May 2016
Revised Date: 13 June 2016

Fund Project: the Science and Technology Commission of Shanghai Municipality 15120503700the National Natural Science Foundation of China 21202099

Figures(8)

A high selective fluorescent probe 4 for cyanides was developed based on the Sonogashira reaction between N-butyl-4-bromo-1, 8-naphthalimide and 2-ethynylbenzaldehyde. In CH₃CN solution, the probe 4 shows moderate colorimetric and fluorescent response to the cyanides. Upon the addition of TBACN, a new peak at 540 nm appeared in the UV-vis spectra accompanied by an instant colorimetric change from colorless to light violet. No change in the spectral pattern of chemosensor 4 was observed in the presence of other anions. Further, chemosensor 4 showed strong fluorescence with the maximum at 484 nm (λ_ex=390 nm) in a mixture of CH₃CN; however, in presence of CN^-, a new emission band (λ_em=600 nm, light brown fluo-rescence) appeared along with a decrease in the emission intensity at 484 nm. Therefore, this process clearly demonstrates that chemosensor 4 can selectively detect cyanide ions by a fluorogenic "on-off" response, which may be attributed to the fact that the electron transfer in 1, 8-naphthalimide is affected by the formation of adducts of anion with carbonyl groups. Moreover, the detailed interference experiments of chemosensor 4 in the mixed solvents were also investigated.
- 1, 8-naphlimide,
- anion recognition,
- cyanides,
- nucleophilic addition,
- fluorescent probe
1. [1]
  Young, C.; Tidwell, L.; Anderson, C. Cyanide:Social, Industrial, and Economic Aspects, The Minerals, Metals & Materials Society, Warrendale, 2001.
2. [2]
  Baud, F. J. Hum. Exp. Toxicol. 2007, 26, 191. doi: 10.1177/0960327107070566
3. [3]
  Koening, R. Science 2000, 287, 1737. doi: 10.1126/science.287.5459.1737
4. [4]
  Vallejos, S.; Estevez, P.; Garcia, F. C.; Serna, F.; Pena, J. L.; Garcia, J. M. Chem. Commun. 2010, 46, 7951. doi: 10.1039/c0cc02143a
5. [5]
  Way, J. L. Annu. Rev. Pharmacol. 1984, 24, 451. doi: 10.1146/annurev.pa.24.040184.002315
6. [6]
  Zamecnik, J.; Tam, J. J. Anal. Toxicol. 1987, 11, 47. doi: 10.1093/jat/11.1.47
7. [7]
  Anderson, R. A.; Harland, W. A. Med., Sci. Law 1982, 22, 35.
8. [8]
  Duke, R. M.; Veale, E. B.; Pfeffer, F. M.; Kruger, P. E.; Gunnlaugsson, T. Chem. Soc. Rev. 2010, 39, 3936. doi: 10.1039/b910560n
9. [9]
  Zhang, Y. M.; Lin, Q.; Wei, T. B.; Li, Y.; Qin, X. P. Chem. Commun. 2009, 45, 6074.
10. [10]
  Du, J.; Hu, M.; Fan, J.; Peng, X. Chem. Soc. Rev. 2012, 41, 4511. doi: 10.1039/c2cs00004k
11. [11]
  Yang, Y.; Zhao, Q.; Feng, W.; Li, F. Chem. Rev. 2013, 113, 192. doi: 10.1021/cr2004103
12. [12]
  Xu, Z.; Kim, S. K.; Yoon, J. Chem. Soc. Rev. 2010, 39, 1457. doi: 10.1039/b918937h
13. [13]
  Hu, J. H.; Yan, N. P.; Chen, J. J.; Li, J. B. Chem. J. Chin. Univ. 2013, 34, 1368 (in Chinese).
14. [14]
  Lin, Q.; Liu, X.; Chen, P.; Wei, T. B.; Zhang, Y. M. Prog. Chem. 2013, 25, 2131 (in Chinese).
15. [15]
  Xu, Z.; Chen, X.; Kim, H. N.; Yoon, J. Chem. Soc. Rev. 2010, 39, 127. doi: 10.1039/B907368J
16. [16]
  Lv, X.; Liu, J.; Liu, Y.; Zhao, Y.; Sun, Y. Q.; Wang, P.; Guo, W. Chem. Commun. 2011, 47, 12843. doi: 10.1039/c1cc15721c
17. [17]
  Ekmekci, Z.; Yilmaz, M. D.; Akkaya, E. U. Org. Lett. 2008, 10, 461. doi: 10.1021/ol702823u
18. [18]
  Chung, Y. M.; Raman, B.; Kim, D. S.; Ahn, K. H. Chem. Commun. 2006, 42, 186.
19. [19]
  Lee, K. S.; Kim, H. J.; Kim, G. H.; Shin, I.; Hong, J. I. Org. Lett. 2008, 10, 49. doi: 10.1021/ol7025763
20. [20]
  Li, H. D.; Li, B.; Jin, L. Y.; Kan, Y. H.; Yin, B. Z. Tetrahedron 2011, 67, 7348. doi: 10.1016/j.tet.2011.07.023
21. [21]
  Jo, J.; Olasz, A.; Chen, C. H.; Lee, D. J. Am. Chem. Soc. 2013, 135, 3620. doi: 10.1021/ja312313f
22. [22]
  Kolosov, D.; Adamovich, V.; Djurovich, P.; Thompson, M. E.; Adachi, C. J. Am. Chem. Soc. 2002, 124, 9945. doi: 10.1021/ja0263588
23. [23]
  Ton, X. A.; Acha, V.; Bonomi, P.; Bui, B. T. S.; Haupt, K. Biosens. Bioelectron. 2015, 64, 359. doi: 10.1016/j.bios.2014.09.017
24. [24]
  Zhu, L.; Yuan, Z.; Simmons, J. T.; Sreenath, K. RSC Adv. 2014, 4, 20398. doi: 10.1039/c4ra00354c
25. [25]
  Xu, Z. C.; Yoon, J.; Spring, D. R. Chem. Soc. Rev. 2010, 39, 1996. doi: 10.1039/b916287a
26. [26]
  Sun, J.-F.; Qian, Y. Chin. J. Org. Chem. 2015, 35, 1104 (in Chinese). doi: 10.6023/cjoc201411008
27. [27]
  Zhang, C.; Ji, K.; Wang, X.; Wu, H.; Liu, C. Chem. Commun. 2015, 51, 8173. doi: 10.1039/C5CC01280E
28. [28]
  Zhou, M.; Chen, J.; Liu, C.; Fu, H.; Zheng, N.; Zhang, C.; Chen, Y.; Cheng, J. Chem. Commun. 2014, 50, 14748. doi: 10.1039/C4CC07308H
29. [29]
  Cai, Y. S.; Guo, Z. Q.; Chen, J. M.; Li, W. L.; Zhong, L. B.; Gao, Y.; Jiang, L.; Chi, L. F.; Tian, H.; Zhu, W. H. J. Am. Chem. Soc. 2016, 138, 2219. doi: 10.1021/jacs.5b11580
30. [30]
  Tomas-Mendivil, E.; Starck, J.; Ortuno, J. C.; Michelet, V. Org. Lett. 2015, 17, 6126. doi: 10.1021/acs.orglett.5b03146
31. [31]
  Scalera, M.; Joyce, A. W. US 2385106, 1945.
32. [32]
  Wang, X.; Silverman, R. B. J. Org. Chem. 1998, 63, 7357. doi: 10.1021/jo980976i
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沈阳化工大学材料科学与工程学院沈阳 110142