DOI QR코드

DOI QR Code

Detection of Nitroaromatic Compounds Based on Fluorescent Silafluorene Chemosensors

  • Kim, Bumseok (Biorefinery Research Center, Korea Research Institute of Chemical Technology)
  • Received : 2010.02.26
  • Accepted : 2010.03.20
  • Published : 2010.03.31

Abstract

A simple and rapid method is described for detecting nitroaromatic explosives in air or seawater with the use of photoluminescent organosilicon compounds. The synthesis, spectroscopic characterization, and fluorescence quenching efficiency of silafluorenes are reported. Silafluorenes were synthesized from the reduction of dilithiobiphenyl with dichlorosilanes. Two silafluorenes were used for the detection of nitroaromatic compounds. Detection of nitroaromatic molecules, such as 2,4-dinitrotoluene (DNT), 2,4,6-trinitrotoluene (TNT), and picric acid (PA), has been explored. A linear Stern-Volmer relationship was observed for the first three analytes. Fluorescence spectra of silafluorenes obtained in either toluene solutions or thin films displayed no shift in the maximum of the emission wavelength. The photoluminescence quenching occurs by a static mechanism.

Keywords

References

  1. D. T. McQuade, A. E. Pullen and T. M. Swager, Chem. Rev. "Conjugated polymer-based chemical sensor" 100, 2537-2574, 2000. https://doi.org/10.1021/cr9801014
  2. K. J. Albert, N. S. Lewis, C. L. Schauer, G. A. Sotzing, S. E. Stitzel, T. P. Vaid and D. R. Walt, Chem. Rev. "Cross-reactive chemical sensor" 100, 2595-2626, 2000. https://doi.org/10.1021/cr980102w
  3. A. M. Rouhi, Chem. Eng. News "Land mines: horrors begging for solutions" 75, 14-22, 1997.
  4. A. Fainberg, Science "Ulysses radio and plasma wave observations in the Jupiter environment" 255, 1531-1537, 1992. https://doi.org/10.1126/science.255.5051.1531
  5. S.-A. Barshick, J. Forensic Sci. "Trace Analysis of Explosives in Seawater Using Solid-Phase Microextraction and Gas Chromatography/Ion Trap Mass Spectrometry" 43, 284-293, 1998.
  6. K. D. Smith, B. R. McCord, W. A. McCrehan, K. Mount and W. F. Rowe, J. Forensic Sci. "Detection of Smokeless Powder Residue on Pipe Bombs by Micellar Electrokinetic Capillary Electrophoresis" 44, 789-794, 1999.
  7. A. W. Czarnik, Nature "A sense for landmines" 394, 417-418, 1998. https://doi.org/10.1038/28728
  8. K. Hakansson, R. V. Coorey, R. A. Zubarev, V. L. Talrose and P. J. Hakansson, Mass Spectrom "Lowmass ions observed in plasma desorption mass spectrometry of high explosives" 35, 337-346, 2000. https://doi.org/10.1002/(SICI)1096-9888(200003)35:3<337::AID-JMS940>3.0.CO;2-7
  9. J. S. Yang and T. M. Swager, J. Am. Chem. Soc. "Na+ Specific Emission Changes in an Ionophoric Conjugated Polymer" 120, 5321-5322, 1998. https://doi.org/10.1021/ja9742996
  10. J. S. Yang and T. M. Swager, J. Am. Chem. Soc. "Fluorescent Porous Polymer Films as TNT Chemosensors: Electronic and Structural Effects" 120, 11864-11873, 1998. https://doi.org/10.1021/ja982293q
  11. H. Sohn, R. M. Calhoun, M. J. Sailor and W. C. Trogler, "Detection of TNT and Picric Acid on Surfaces and in Seawater by Using Photoluminescent Polysiloles" Angew. Chem. Int. Ed., vol. 11, pp. 2104-2105, 2001.
  12. H. Sohn, M. J. Sailor, D. Magde and W. C. Trogler, "Detection of Nitroaromatic Explosives Based on Photoluminescent Polymers Containing Metalloles" J. Am. Chem. Soc., vol 125, pp. 3821-3830, 2003. https://doi.org/10.1021/ja021214e
  13. W. H. Dennis and D. H. Rosenblatt, J. Chem. Eng. Data "Improved synthesis of TNT isomers" 20, 202-203, 1975. https://doi.org/10.1021/je60065a016