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Synthesis and study of optical application of organic dyes based on substituted 4-oxo-2-(thiophen-2-yl)aminobut-2-enoic acids
Russian version
Gorbunova I. A. 1, Klimenko D.I. 1, Rider M.A.1, Denislamova E. S. 2, Shipilovskikh D. A.2,3, Cherevkov S. A.1, Shipilovskikh S. A.1
1International research and educational center for physics of nanostructures, ITMO University, Saint-Petersburg, Russia
2Perm Research Polytechnic University, Perm, Russia
3Peter the Great Saint-Petersburg Polytechnic University, St. Petersburg, Russia
PDF
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.
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