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Triphenylbenzene Sensor for Selective Detection of Picric Acid

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Abstract

A C 3-symmetric triphenylbenzene based photoluminescent compound, 1,3,5-tris(4′-(N-methylamino)phenyl) benzene ([NHMe]3TAPB), has been synthesized by mono-N-methylation of 1,3,5-tris(4′-aminophenyl) benzene (TAPB) and structurally characterized. [NHMe]3TAPB acts as a selective fluorescent sensor for picric acid (PA) with a detection limit as low as 2.25 ppm at a signal to noise ratio of 3. Other related analytes (i.e. TNT, DNT and DNB) show very little effect on the fluorescence intensity of [NHMe]3TAPB. The selectivity is triggered by proton transfer from picric acid to the fluorophore and ground-state complex formation between the protonated fluorophore and picrate anion through hydrogen bonding interactions. The fluorescence lifetime measurements reveal static nature of fluorescence quenching.

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Acknowledgements

The authors thank DST/SERB, New Delhi for financial support (No. SB/S1/IC-48/2013) and SERB, New Delhi for J. C. Bose Fellowship (SB/S2/JCB-85/2014). SN thanks DST and PV thanks CSIR for research fellowships.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076, India

    S. Nagendran, Pratap Vishnoi & Ramaswamy Murugavel

Authors
  1. S. Nagendran
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  2. Pratap Vishnoi
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  3. Ramaswamy Murugavel
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Corresponding author

Correspondence to Ramaswamy Murugavel.

Electronic supplementary material

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(DOCX 1.37 mb)

NMR, mass, FT-IR, UV-Vis, additional photoluminescence spectra, Benesi-Hildebrand (B-H) plots, fluorescence quenching profiles of [NHMe]3TAPB (3) with other polynitroaromatic analytes (TNT, DNT and DNB) and crystal information file (CIF). A copy of CIF can be obtained free of charge on quoting the depository numbers CCDC 1510759–1,510,760.

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Nagendran, S., Vishnoi, P. & Murugavel, R. Triphenylbenzene Sensor for Selective Detection of Picric Acid. J Fluoresc 27, 1299–1305 (2017). https://doi.org/10.1007/s10895-017-2063-9

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  • DOI: https://doi.org/10.1007/s10895-017-2063-9

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