Citation: Chen Kai, Han Baichuan, Ji Sixin, Sun Jin, Gao Zhenzhong, Hou Xianfeng. A Ratiometric Fluorescence Probe for Detecting Gaseous Isocyanates Directly[J]. Acta Chimica Sinica, ;2019, 77(4): 365-370. doi: 10.6023/A18120484 shu

A Ratiometric Fluorescence Probe for Detecting Gaseous Isocyanates Directly

South China Agricultural University, College of Material and Energy, Guangzhou 510640

Corresponding author: Gao Zhenzhong, zzgaoscau@163.com Hou Xianfeng, xfhou@scau.edu.cn
Received Date: 4 December 2018
Available Online: 1 May 2019
Fund Project: the Guangzhou Science and Technology Plan 201803030031the Natural Science Foundation of Guangdong Province, China 2018A030310348Project supported by the Natural Science Foundation of Guangdong Province, China (No. 2018A030310348), and the Guangzhou Science and Technology Plan (No. 201803030031)

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Isocyanates is a widely-used chemical in many manufacturing industries, such as polymer industry, pharmaceutical production and production of a variety of agricultural chemicals. However, it is harmful to human health due to the volatility. Therefore, it is necessary to develop methods to detect isocyanates quickly and conveniently, especially to gaseous isocyanates. In this work, a novel fluorescent probe, N-buty-4-hydroxy-1, 8naphthalimide, was developed for detection of isocyanates. This fluorescence probe can be synthesized by a simple three-steps synthetic route, and the overall yield of the whole synthesizing process reached 75%. In the absence of isocyanate, the probe solution displays an emission centering at 596 nm when excited at 370 nm, which is yellow to the naked eye. Once isocyanate is added, the fluorescence of solution changes from yellow to blue, and the process finishes in 4 min. The detecting limit of this probe to isocyanates is calculated to be 112 nmol·L^-1. It is also proved that this probe possesses excellent selectivity for isocyanate and distinct anti-interference to common organic volatilized compounds. In addition, the reaction mechanism between the probe and isocyanate were proved by HPLC, NMR and ESI-MASS. Results show that the hydroxy group on the 4th position of naphthalene ring of probe reacts with isocyanate group (-NCO) of isocyanate, and resulting in carbamates, which alter 4th substituent group of probe molecule and lead to change of fluorescence. In order to detect the gaseous isocyanates directly, test paper are developed based on N-buty-4-hydroxy-1, 8naphthalimide. When the test paper exposed to isocyanates vapor, the yellow fluorescence fade away gradually and a blue fluorescence appear in 6 min. And the test paper possesses excellent selectivity for gaseous isocyanate and distinct anti-interference to common VOCs. In conclusion, this strategy is an efficient way to detect gaseous isocyanates, and it may provide a referable approach for directly monitoring the volatile organic compounds in air.
- isocyanates,
- fluorescence probe,
- testing paper
1. [1]
  Xuan, L. M. S. Thesis, North China University of Science and Technology, Tangshan, 2015(in Chinese).
2. [2]
  Tang, Y. F. M. S. Thesis, Anhui Jianzhu University, Hefei, 2013(in Chinese).
3. [3]
  Spindler, R.; Frechet, J. M. J. Macromolecules 1993, 26, 4809. doi: 10.1021/ma00070a013
4. [4]
  Xie, W.-Q.; Chai, X.-S. J. Chromatogr. A 2016, 1468, 241. doi: 10.1016/j.chroma.2016.09.042
5. [5]
  Kubitz, K. A. Anal. Chem. 1957, 29, 814. doi: 10.1021/ac60125a023
6. [6]
  Kormos, L. H.; Sandridge, R. L.; Keller, J. Anal. Chem. 1981, 53, 1122. doi: 10.1021/ac00230a046
7. [7]
  Budnik, L. T.; Nowak, D.; Merget, R.; Lemiere, C.; Baur, X. J. Occup. Med. Toxicol. 2011, 6, 9. doi: 10.1186/1745-6673-6-9
8. [8]
  Coldwell, M.; White, J. UK Health and Safety Laboratory, Buxton, 2005.
9. [9]
  Agarwal, B.; Jurschik, S.; Sulzer, P. Rapid Commun. Mass Spectrom. 2012, 26, 983. doi: 10.1002/rcm.6173
10. [10]
  Andre, C.; Jorge, F.; Castanheira, I.; Matos, A. J. Chemometr. 2013, 27, 91. doi: 10.1002/cem.v27.5
11. [11]
  Karlsson, D. Anal. Chim. Acta 2005, 534, 263. doi: 10.1016/j.aca.2004.11.049
12. [12]
  NIOSH Pocket Guide to Chemical Hazards and Other Databases. DHHS(NIOSH) Publication No. 2001-145(2001).
13. [13]
  Skarping, G.; Renman, L.; Smith, B. E. F. J. Chromatogr. A 1983, 267, 315. doi: 10.1016/S0021-9673(01)90851-9
14. [14]
  Sharping, G.; Sango, C.; Smith, B. E. F. J. Chromatogr. A 1981, 208, 313. doi: 10.1016/S0021-9673(00)81943-3
15. [15]
  Dunlap, K. L.; Sandridge, R. L.; Keller, J. Anal. Chem. 1976, 48, 497. doi: 10.1021/ac60367a043
16. [16]
  Gagne, S.; Lesage, J.; Ostiguy, C.; Van Tra, H. Analyst 2003, 128, 1447. doi: 10.1039/B310463J
17. [17]
  Warwick, C. J.; Bagon, D. A.; Purnell, C. J. Analyst 1981, 106, 676. doi: 10.1039/an9810600676
18. [18]
  Ghosh, K. R.; Saha, S. K.; Gao, J.-P.; Wang, Z.-Y. Chem. Commun. 2014, 50, 1886. doi: 10.1039/c3cc48311h
19. [19]
  Gao, Z.-Z.; Han, B.-C.; Chen, K. Chem. Commun. 2017, 53, 6231. doi: 10.1039/C7CC02269G
20. [20]
  Chen, Q.; Bian, N.; Cao, C.; Qiu, X.-L.; Qi, A.-D.; Han, B.-H. Chem. Commun. 2010, 46, 4067. doi: 10.1039/c002894k
21. [21]
  Li, Q.-Q.; Li, Z. Adv. Sci. 2017, 4, 1600484. doi: 10.1002/advs.v4.7
22. [22]
  Chen, J.; Zhang, C.-H.; Lv, K.; Wang, H.; Zhang, P.-S.; Yi, P.-G.; Jiang, J.-H. Sensor. Actuat. B 2017, 251, 533. doi: 10.1016/j.snb.2017.05.072
23. [23]
  Daniela, G.; Alicia, V. V.; Denis, B.; Angel, G. B. J. Nanophotonics 2018, 12, 012505.
24. [24]
  Zhang, G.-X.; Hu, F.; Zhang, D.-Q. Langmuir 2015, 31, 4593. doi: 10.1021/la5029367
25. [25]
  Sun, C.-L.; Teng, K.-X.; Niu, L.-Y.; Chen, Y.-Z.; Yang, Q.-Z. Acta Chim. Sinica 2018, 76, 779(in Chinese). doi: 10.7503/cjcu20170368
26. [26]
  Wang, J.; Wu, Y.-L.; Sun, L.-H.; Zeng, F.; Wu, S.-Z. Acta Chim. Sinica 2016, 74, 910(in Chinese).
27. [27]
  Liu, Z.; He, W.; Guo, Z. Chem. Soc. Rev. 2013, 42, 1568. doi: 10.1039/c2cs35363f
28. [28]
  Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 20, 3.
29. [29]
  Zheng, X.-J.; Zhu, W.-C.; Liu, D.; Ai, H. Appl. Mater. Interfaces 2014, 6, 7996. doi: 10.1021/am501546h
30. [30]
  Lin, H.-H.; Chan, Y.-C.; Chen, J.-W. J. Mater. Chem. 2011, 21, 3170. doi: 10.1039/c0jm02942d
31. [31]
  Leng, B.; Jiang, J.-B.; Tian, H. AlChE J. 2010, 56, 2957. doi: 10.1002/aic.v56:11
32. [32]
  Kai, Y.-M.; Hu, Y.-H.; Wang, K.; Zhi, W.-B.; Liang, M.-M.; Yang, M. Spectrochim. Acta A 2014, 118, 239. doi: 10.1016/j.saa.2013.08.100
33. [33]
  Zhang, H.-F.; Liu, T.; Yin, C.-C.; Wen, Y.; Chao, J.-B.; Zhang, Y.-B.; Huo, F.-J. Spectrochim. Acta A 2017, 174, 230. doi: 10.1016/j.saa.2016.11.039
34. [34]
  Li, B.; Yu, Y.-L.; Xiang, F.-Q.; Zhang, S.-Y. Appl. Mater. Interfaces 2018, 10, 16282. doi: 10.1021/acsami.8b02539
35. [35]
  Guo, B.-P.; Pan, X.-Z.; Liu, Y.-F.; Nie, L.-X.; Zhao, H.-Z.; Liu, Y.-Z.; Jing, J.; Zhang, X.-L. Sensor. Actuat. B-Chem. 2018, 256, 632. doi: 10.1016/j.snb.2017.09.196
36. [36]
  Zhang, Z.; Fan, J.-L.; Zhao, Y.-H.; Kang, Y.; Du, J.-J.; Peng, X.-J. ACS Sens. 2018, 3, 735 doi: 10.1021/acssensors.8b00082
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