TY - JOUR

T1 - Fluorescent scaffold integrating 2-aryl-1,2,3-triazole and thiazole rings with tuneable optical properties. Fundamental aspects and application prospects

AU - Krasilnikov, Vitalii A.

AU - Fomin, Timur O.

AU - Vargina, Maria V.

AU - Minin, Artem S.

AU - Slepukhin, Pavel A.

AU - Benassi, Enrico

AU - Belskaya, Nataliya P.

N1 - Сведения о финансировании Финансирующий спонсор Номер финансирования Акроним Ministry of Education and Science of the Russian Federation Minobrnauka Nazarbayev University NU Текст о финансировании Research funding from the Ministry of Science and Higher Education of the Russian Federation (Ural Federal University Development Programme within the Priority 2030 Programme) is gratefully acknowledged. This work was carried out using the equipment of the Shared Research Centre of Scientific Equipment SRC IIP UrB RAS. Computing resources were kindly provided by the HPCC of Nazarbayev University.

PY - 2025/3/1

Y1 - 2025/3/1

N2 - A fluorescent scaffold was designed and synthesised by the conjugating of the 1,2,3-triazole ring with aryl- or diarylthiazole systems. As a result, two series of thiazole-1,2,3-triazole fluorophores were prepared by the Hantzsch reaction and Suzuki-Miyaura coupling, namely 4-aryl-2-(2-aryl-2H-1,2,3-triazol-4-yl)thiazole (DATTs) and 4,5-diaryl-2-(2-aryl-2H-1,2,3-triazol-4-yl)thiazole (TATTs). Their structures were investigated by XRD and quantum mechanical calculations at DFT level. All the novel compounds were studied under different conditions by UV–vis absorption and fluorescent spectroscopy and TD-DFT calculations. Strong solvato(fluoro)chromism was registered, resulting in a two- or three colour fluorescence depending on solvent polarity, accompanied by an increase in emission intensity when solvent polarity increases. Concentration dependent emissions were found, and DATTs and TATTs exhibited red-shifted absorption and emission compared to the parent triazoles and sensitivity to polar media. Biological tests demonstrated the biocompatibility of the synthesised fluorophores and their low or null toxicity. Multicolour fluorescence of DATTs and TATTs as a function of the excitation wavelength and dye localisation was demonstrated in cell experiments.

AB - A fluorescent scaffold was designed and synthesised by the conjugating of the 1,2,3-triazole ring with aryl- or diarylthiazole systems. As a result, two series of thiazole-1,2,3-triazole fluorophores were prepared by the Hantzsch reaction and Suzuki-Miyaura coupling, namely 4-aryl-2-(2-aryl-2H-1,2,3-triazol-4-yl)thiazole (DATTs) and 4,5-diaryl-2-(2-aryl-2H-1,2,3-triazol-4-yl)thiazole (TATTs). Their structures were investigated by XRD and quantum mechanical calculations at DFT level. All the novel compounds were studied under different conditions by UV–vis absorption and fluorescent spectroscopy and TD-DFT calculations. Strong solvato(fluoro)chromism was registered, resulting in a two- or three colour fluorescence depending on solvent polarity, accompanied by an increase in emission intensity when solvent polarity increases. Concentration dependent emissions were found, and DATTs and TATTs exhibited red-shifted absorption and emission compared to the parent triazoles and sensitivity to polar media. Biological tests demonstrated the biocompatibility of the synthesised fluorophores and their low or null toxicity. Multicolour fluorescence of DATTs and TATTs as a function of the excitation wavelength and dye localisation was demonstrated in cell experiments.

KW - 1,2,3-triazole-thiazole assembly

KW - Aggregation enhancement emission

KW - Excitation-dependent fluorescence

KW - TD DFT calculations

KW - Viscosity sensitivity

UR - https://www.mendeley.com/catalogue/b20d61b7-5de3-33d6-a973-49397afde088/

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85208595763&origin=inward&txGid=a20280c3b3ebd8d2e6fd68596ed76bfb

U2 - 10.1016/j.jphotochem.2024.116104

DO - 10.1016/j.jphotochem.2024.116104

M3 - Article

VL - 460

JO - Journal of Photochemistry and Photobiology A: Chemistry

JF - Journal of Photochemistry and Photobiology A: Chemistry

SN - 1010-6030

M1 - 116104

ER -