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Molecules 2018, 23(11), 2861; https://doi.org/10.3390/molecules23112861

Spectroscopic Studies of Dual Fluorescence in 2-(4-Fluorophenylamino)-5-(2,4-dihydroxybenzeno)-1,3,4-thiadiazole: Effect of Molecular Aggregation in a Micellar System

1
Department of Biophysics, University of Life Sciences in Lublin, Akademicka 13, 20-950 Lublin, Poland
2
Department of Analytical Chemistry (C1), Faculty of Chemical Engineering and Technology, Krakow Technical University, Warszawska 24, 31-155 Krakow, Poland
3
Department of Physical Biochemistry, Faculty of Biochemistry, Biophysics and Biotechnology of the Jagiellonian University, Gronostajowa 7, 30-387 Krakow, Poland
4
Department of Analysis and Differential Equations, Faculty of Mathematics and Computer Science, University of Warmia and Mazury, Słoneczna 54, PL-10-710 Olsztyn, Poland
5
Department of Physical Chemistry–Interfacial Phenomena, Faculty of Chemistry, Maria Curie–Sklodowska University, 20-031 Lublin, Poland
6
Department of Applied Physics, Lublin University of Technology, Nadbystrzycka 38, 20-618 Lublin, Poland
7
Institute of Industrial Organic Chemistry, Annopol 6, 03-236 Warsaw, Poland
8
Department of Chemistry, University of Life Sciences in Lublin, 20-950 Lublin, Poland
*
Author to whom correspondence should be addressed.
Received: 24 October 2018 / Accepted: 31 October 2018 / Published: 2 November 2018
(This article belongs to the Section Photochemistry)
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Abstract

The article presents the results of spectroscopic studies focused on a selected compound from the 1,3,4-thiadiazole group—2-(4-fluorophenylamino)-5-(2,4-dihydroxybenzeno)-1,3,4-thia-diazole (FABT)—in a micellar system formed by Triton X-100, a non-ionic detergent. Fluorescence measurements revealed the phenomenon of dual fluorescence whose emergence is related to the particular molecular organisation of the compound, which depends both on the concentration of the detergent and, most of all, the concentration of the compound itself. Dual fluorescence of FABT in a micellar system was observed for the compound dissolved in a methanol aqueous system, i.e., an environment wherein the dual fluorescence of the compound had never been reported before. Based on the interpretation of UV-Vis electronic absorption, resonance light scattering (RLS), emission and excitation fluorescence spectra, as well as measurements of dynamic light scattering (DLS) and Principal Component Analysis (PCA), we were able to relate the occurrence of this effect to the process of molecular aggregation taking place between FABT molecules in the micellar system in question. Results of fluorescence spectra measurements and time-correlated single photon counting (TCSPC) indicate that dual fluorescence occurs at detergent concentrations necessary to form micellar systems, which in turn facilitate the process of aggregation of FABT molecules. The correlation between the observed fluorescence effects and the previous measurements performed for analogues from this group suggests the possibility of charge transfer (CT) within the range of detergent concentrations wherein the aforementioned fluorescence effects are observed. It ought to be emphasised that this type of fluorescence effects are relatively easy to induce, which predisposes this groups of fluorophores as ideal fluorescence probes in the context of biological samples. View Full-Text
Keywords: 1,3,4-thiadiazole; molecular spectroscopy; molecular aggregation; induced dual fluorescence effects; micellar systems 1,3,4-thiadiazole; molecular spectroscopy; molecular aggregation; induced dual fluorescence effects; micellar systems
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Czernel, G.; Matwijczuk, A.; Karcz, D.; Górecki, A.; Niemczynowicz, A.; Szcześ, A.; Gładyszewski, G.; Matwijczuk, A.; Gładyszewska, B.; Niewiadomy, A. Spectroscopic Studies of Dual Fluorescence in 2-(4-Fluorophenylamino)-5-(2,4-dihydroxybenzeno)-1,3,4-thiadiazole: Effect of Molecular Aggregation in a Micellar System. Molecules 2018, 23, 2861.

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