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Optics and Spectroscopy, 2024 Volume 132, Issue 7, Pages 747–754 (Mi os1226)

Spectroscopy of condensed matter

Synthesis and study of optical application of organic dyes based on substituted 4-oxo-2-(thiophen-2-yl)aminobut-2-enoic acids

I. A. Gorbunovaa, D. I. Klimenkoa, M. A. Ridera, E. S. Denislamovab, D. A. Shipilovskikhbc, S. A. Cherevkova, S. A. Shipilovskikha

a International Research and Educational Center for Physics of Nanostructures, ITMO University, St. Petersburg, Russia
b Perm Research Polytechnic University, Perm, Russia
c Peter the Great St. Petersburg Polytechnic University, St. Petersburg, Russia

Abstract: Highly photoluminescent organic dyes are key materials for organic optoelectronics and photonics. In this paper, we report on the rational design of organic dyes based on substituted 2-(thiophen-2-yl)amino-4-oxobut-2-enoic acids, which are synthesised by a sequential multistep method from substituted 2-hydroxy-4-oxobut-2-enoic acids and the ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-carboxylate. The ability of modification of the chemical structure of the dyes during synthesis allows the introduction of different structural fragments that have a significant effect on the optical properties of the target materials. The obtained organic dyes possess effective photoluminescence (PL) in the orange-red region of the spectrum from 596 to 635 nm in powdered form. At the same time, solvents convert them to a non-luminescent state, and a red shift of the main absorption maximum occurs during the transition from nonpolar to polar solvents, which suggests a significant influence of the formed hydrogen bonds inside the molecule during the formation of a rigid crystal structure.

Keywords: organic dyes, photoluminescence, substituted 2, 4-dioxobutanoic acids, 2-aminothiophenes.

Received: 27.04.2024
Revised: 05.06.2024
Accepted: 05.06.2024

DOI: 10.61011/OS.2024.07.58898.6445-24



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