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Excited State Intramolecular Proton Transfer (ESIPT)-Based Sensor for Ion Detection

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Abstract

C-2 and C-5 substituted imidazole skeleton was synthesized through a one-pot two-step strategy. Synthesized molecule emits the light on ESIPT (excited-state intramolecular proton transfer). This molecule was utilized for its proton donor ability, and we have observed that fluoride and cyanide ions can be detected selectively. Different cations and anions were selected to observe the response of the synthesized molecule. However, there were not any fluorometric and colorimetric response except for fluoride and cyanide ions. Detection limits of fluoride and cyanide ions were found to be 9.22 μM and 11.48 μM, respectively. 1H-NMR spectra for the solution of the sensor and TBAF (tetrabuthylammoniumfluoride) were used for the identification of [L]−[HF2]− species. 3 equiv. TBAF saturated the solution of the sensor in d6-DMSO, and some of the proton resonances shifted to upfield due to the through-bond effect. The disappearance of NH proton with 0.5 equiv. TBAF or TBACN (tetrabuthylammoniumcyanide) showed that there was a proton abstraction by fluoride and cyanide ions, instead of the hydrogen bond. Solid-state application was utilized, and paper test strips were applied. Emission differences emerged when the sensor loaded strips were reacted with TBAF. Time resolved experiments revealed that solution of the sensor and TBAF in DMSO have multiexponential decay, and one of the lifetime was measured as 13.4 ns.

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Acknowledgments

Authors thank to the Scientific and Technological Research Council of Turkey (TUBITAK) for funding the study. NMR data was taken from Science Research and Application Center of Van YYÜ. For this reason, the authors are thankful to the head of the center.

Funding

This study was funded by TÜBİTAK (grand number:115Z112).

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Authors and Affiliations

  1. Pharmaceutical Chemistry Section, Van Yuzuncu Yil University, 65080, Van, Turkey

    Burak Kuzu, Meltem Tan & Nurettin Menges

  2. SAFF Chemical Reagent R&D Laboratory, VAN-TEKNOKENT, Campus, 65080, Van, Turkey

    Burak Kuzu, Meltem Tan & Nurettin Menges

  3. Department of Biomedical Engineering, Isparta University of Applied Sciences, 32260, Isparta, Turkey

    Zeynep Ekmekci

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Burak Kuzu and Meltem Tan progressed experiments, Zeynep Ekmekci made measurements of absorbance and fluorescence experiments, Nurettin Menges organized the theoretical and experimental results, and wrote the manuscript. All authors proved the final version of the manuscript.

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Correspondence to Nurettin Menges.

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Kuzu, B., Ekmekci, Z., Tan, M. et al. Excited State Intramolecular Proton Transfer (ESIPT)-Based Sensor for Ion Detection. J Fluoresc 31, 861–872 (2021). https://doi.org/10.1007/s10895-021-02716-1

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