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

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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.

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

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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.

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Authors and Affiliations

  1. School of Chemical & Biotechnology, SASTRA University, Thanjavur, 613401, Tamil Nadu, India

    P. S. Hariharan & Savarimuthu Philip Anthony

  2. School of Science and Humanities, Department of Chemistry, Karunya University, Coimbatore, 641 114, Tamil Nadu, India

    J. Pitchaimani & Vedichi Madhu

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  1. P. S. Hariharan
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  2. J. Pitchaimani
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  3. Vedichi Madhu
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  4. Savarimuthu Philip Anthony
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Correspondence to Vedichi Madhu or Savarimuthu Philip Anthony.

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Hariharan, P.S., Pitchaimani, J., Madhu, V. et al. Perylene Diimide Based Fluorescent Dyes for Selective Sensing of Nitroaromatic Compounds: Selective Sensing in Aqueous Medium Across Wide pH Range. J Fluoresc 26, 395–401 (2016). https://doi.org/10.1007/s10895-015-1725-8

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