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“Seems Bad Turns Good” – traces of precursor in dicationic ionic liquid lead to analytical application

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Abstract

We explored a geminal dicationic ionic liquid (DCIL), 1′-(propane-1,3-diyl)bis(4-aminopyridin-1-ium) dibromide, [C3(Amp)2][Br]2, as a fluorescent probe for detection of hydroquinone (HQ). The DCIL, undesirably, was found to incorporate trace precursor (4-aminopyridine). The impurity in DCIL was identified by nuclear magnetic resonance (NMR) spectroscopy and quantified by high-performance liquid chromatography. Surprisingly, trace precursor associated with the sensor actually assisted the quenching process by providing essential in situ mild alkaline environment. The proposed detection method depends on significant quenching of fluorescence of DCIL with increasing concentration of HQ. A plausible quenching mechanism involving photoinduced charge transfer is discussed. The DCIL probe offers a wide detection range of 1–800 µM with detection limit of 0.38 µM for HQ. These results highlight the concept of beneficial intentional doping of impurities in sensing material that does not alter its inherent physicochemical properties but might improve its performance.

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Acknowledgements

S.K.P. and M.M.V. under the UGC-BSR Meritorious Students fellowship and S.C.B. under RGNF are grateful to the University Grants Commission (UGC), New Delhi, India, for financial support and instrument facilities at the Department of Chemistry, Shivaji University, Kolhapur. This work is partially supported by Human Resources Development program (no. 20124010203180) of the Korea Institute of Energy Technology Evaluation and Planning (KETEP) grant, funded by the Korea Government Ministry of Trade, Industry, and Energy.

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Authors and Affiliations

  1. Analytical Chemistry and Material Science Research Laboratory, Department of Chemistry, Shivaji University, Kolhapur, MS, 416004, India

    Sandip K. Patil, Sagar C. Bhise, Deepak V. Awale, Madagonda M. Vadiyar, Suryakant A. Patil, Uma V. Ghorpade & Sanjay S. Kolekar

  2. Fluorescence Spectroscopy Research Laboratory, Department of Chemistry, Shivaji University, Kolhapur, MS, 416004, India

    Dattatray B. Gunjal & Govind B. Kolekar

  3. Department of Materials Science and Engineering, Chonnam National University, Gwangju, 500 757, South Korea

    Uma V. Ghorpade & Jin H. Kim

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  1. Sandip K. Patil
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Electronic supplementary material

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11164_2018_3489_MOESM1_ESM.docx

Electronic Supplementary Material includes 1H and 13C NMR spectra for DCIL-1 (Fig. S1-S2); HPLC method for detection of trace 4-Amp; Chromatograms of 4-Amp and DCIL-1 obtained from HPLC analysis (Fig. S3); UV–Vis absorption spectra of 0.01 mol L−1 DCIL-1 in presence of a series of different concentrations of HQ (Fig. S4); Absorbance spectrum of HQ and emission spectrum of DCIL-1 to check the possibility of spectral overlap (Fig. S5); Fluorescence spectra of 0.01 mol L−1 DCIL-1 in presence of different concentrations (10–1000 µM) of p-benzoquinone (BQ) (Fig. S6). (DOCX 1214 kb)

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Patil, S.K., Bhise, S.C., Awale, D.V. et al. “Seems Bad Turns Good” – traces of precursor in dicationic ionic liquid lead to analytical application. Res Chem Intermed 44, 6267–6282 (2018). https://doi.org/10.1007/s11164-018-3489-7

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