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The syntheses, photophysical properties and pH-sensitive studies of heterocyclic azo dyes bearing coumarin–thiophene–thiazole

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Abstract

This study reports the synthesis of two novel thiazolylazo dyes (4 and 5) bearing coumarin–thiophene moiety. UV–Vis spectroscopy was used to investigate the photophysical properties of 4 and 5 in different solvents. The dyes displayed good potential for hydroxide sensing in different mediums. The reversibility was also studied, and it was found that 4 and 5 could be reverted to their original state by adding acid. Furthermore, the acidochromic properties were studied in protic and aprotic media. Both dyes displayed a good acidochromic response in DCM. Moreover, 4 and 5 were investigated for pH sensing, and it was found that both compounds displayed changes in absorption spectra in a basic media. The theoretical calculations were carried out to investigate the deprotonation and protonation mechanisms using density functional theory (DFT). The thermal properties of the dyes were investigated using thermogravimetric analysis (TGA). The results showed good thermal stability up to around 200 °C.

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Acknowledgements

The numerical calculations reported in this paper were fully performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Gazi University, Yenimahalle, 06560, Ankara, Turkey

    Mohamed Yahya, Rumeysa Metin, Burcu Aydıner & Zeynel Seferoğlu

  2. Department of Chemistry, University of Nevada, Reno, 1664N. Virginia St, Reno, NV, 89557, USA

    Mohamed Yahya

  3. Technological Dyes and Materials Application and Research Center (TEBAM), Gazi University, 06560, Ankara, Turkey

    Burcu Aydıner, Nurgül Seferoğlu & Zeynel Seferoğlu

  4. Department of Advanced Technology, Graduate School of Natural and Applied Sciences, Gazi University, Yenimahalle, 06560, Ankara, Turkey

    Nurgül Seferoğlu

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The authors confirm contribution to the paper as follows: study conception and design: ZS; data collection: MY, RM; analysis and interpretation of results: BA, NS; draft manuscript preparation: MY, RM, and BA. All the authors reviewed the results and approved the final version of the manuscript.

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Yahya, M., Metin, R., Aydıner, B. et al. The syntheses, photophysical properties and pH-sensitive studies of heterocyclic azo dyes bearing coumarin–thiophene–thiazole. ANAL. SCI. 39, 829–842 (2023). https://doi.org/10.1007/s44211-023-00281-0

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