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Photophysical and Fluorescence Nitroaromatic Sensing Properties of Methylated Derivative of a Pamoic Acid Ester

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Abstract

Rapid and selective detection of nitroaromatic explosives is very important for public safety, life, and environmental health. Current instrumental techniques suffer from high cost and poor site used. In order to investigate fluorescence sensing of nitroaromatics, we prepare a new small fluorescence probe derived from pamoic acid. This study covers the synthesis of Pamoic acid based [diisopropyl 4,4'-methylenebis(3-methoxy-2-naphthoate)] (2) material and characterization of its structure. The methylation of Pamoic acid ester, which we have successfully synthesized in our previous studies, was carried out in this study. Determination of the photophysical and fluorescent nitroaromatic detection properties of the compound forms the basis of the study. Structural characterization of the synthesized compound [diisopropyl 4,4'-methylenebis(3-methoxy-2-naphthoate)] (2) was characterized using spectroscopic methods. In addition, Molecular structure of the synthesized compound was determined by single crystal X-ray diffraction studies. In the final step, compounds [diisopropyl 4,4'-methylenebis(3-hydroxy-2-naphthoate)] (1) and [diisopropyl 4,4'-methylenebis(3-methoxy-2-naphthoate)] (2) were tested as fluorescent probes for the detection of some nitroaromatic explosives. It is seen that Nitrobenzene provides the best quenching effect on the compound [diisopropyl 4,4'-methylenebis(3-hydroxy-2-naphthoate)] (1) containing the -OH group, with lowest the limit of detection (LOD) value. It was observed that Picric acid provided the best quenching effect with lowest the limit of detection (LOD) value in the compound [diisopropyl 4,4'-methylenebis(3-methoxy-2-naphthoate)] (2) obtained by methylation of the -OH group in the compound [diisopropyl 4,4'-methylenebis(3-hydroxy-2-naphthoate)] (1).

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Authors and Affiliations

  1. Department of Materials Science and Engineering, Kahramanmaras Sutcu Imam University, Kahramanmaraş, 46100, Turkey

    Mustafa Bal

  2. Chemistry Department, Kahramanmaras Sutcu Imam University, Kahramanmaraş, 46100, Turkey

    Mustafa Bal & Muhammet Köse

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  1. Mustafa Bal
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  2. İrfan Şahin
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  3. Muhammet Köse
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Contributions

All authors contributed to the study conception and design. Material preparation, data collection and analysis were performed by MB and İŞ. Data interpretation was done by MB, İŞ and MK. The first draft of the manuscript was written by MB, İŞ and MK. All authors read and approved the final manuscript.

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Correspondence to Mustafa Bal.

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Bal, M., Şahin, İ. & Köse, M. Photophysical and Fluorescence Nitroaromatic Sensing Properties of Methylated Derivative of a Pamoic Acid Ester. J Fluoresc 33, 77–90 (2023). https://doi.org/10.1007/s10895-022-03038-6

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