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Journal of Fluorescence

, Volume 26, Issue 2, pp 395–401 | Cite as

Perylene Diimide Based Fluorescent Dyes for Selective Sensing of Nitroaromatic Compounds: Selective Sensing in Aqueous Medium Across Wide pH Range

  • P. S. Hariharan
  • J. Pitchaimani
  • Vedichi Madhu
  • Savarimuthu Philip Anthony
ORIGINAL ARTICLE

Abstract

Water soluble perylenediimide based fluorophore salt, N,N′-bis(ethelenetrimethyl ammoniumiodide)-perylene-3,4,9,10-tetracarboxylicbisimide (PDI-1), has been used for selective fluorescence sensing of picric acid (PA) and 4-nitroaniline (4-NA) in organic as well as aqueous medium across wide pH range (1.0 to 10.0). PDI-1 showed strong fluorescence in dimethylformamide (DMF) (Φf = 0.26 (DMF) and moderate fluorescence in water. Addition of picric acid (PA) and 4-nitroaniline (4-NA) into PDI-1 in DMF/aqueous solution selectively quenches the fluorescence. The concentration dependent studies showed decrease of fluorescence linearly with increase of PA and 4-NA concentration. The interference studies demonstrate high selectivity for PA and 4-NA. Interestingly, PDI-1 showed selective fluorescence sensing of PA and 4-NA across wide pH range (1.0 to 10.0). Selective fluorescence sensing of PA and 4-NA has also been observed with trifluoroacetate (PDI-2), sulfate (PDI-3) salt of PDI-1 as well as octyl chain substituted PDI (PDI-4) without amine functionality. These studies suggest that PA and 4-NA might be having preferential interaction with PDI aromatic core and quenches the fluorescence. Thus PDI based dyes have been used for selective fluorescent sensing of explosive NACs for the first time to the best our knowledge.

Graphical Abstract

Selective fluorescent sensing of picric acid and 4-nitroaniline nitroaromatic compounds by perylene diimide fluorescent dyes

Keywords

Perylene diimide Fluorescent sensor Explosive sensor Picric acid sensor 

Notes

Acknowledgments

Financial support from the Department of Science and Technology, New Delhi, India (DST Fast Track scheme no. SR/FT/CS-03/2011(G), SB/FT/CS-182/2011) is acknowledged with gratitude. We thank CRF, SASTRA University for UV-Visible spectrophotometer. The authors gratefully acknowledge the modern lab facility by Karunya University.

Supplementary material

10895_2015_1725_MOESM1_ESM.docx (2 mb)
ESM 1 (DOCX 2005 kb)

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  1. 1.School of Chemical & BiotechnologySASTRA UniversityThanjavurIndia
  2. 2.School of Science and Humanities, Department of ChemistryKarunya UniversityCoimbatoreIndia

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