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RAS Chemistry & Material ScienceЖурнал общей химии Russian Journal of General Chemistry

  • ISSN (Print) 0044-460X
  • ISSN (Online) 3034-5596

Synthesis of new efficient fluorophores of thieno[2,3-b]pyridine series

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PII
10.31857/S0044460X23080061-1
DOI
10.31857/S0044460X23080061
Publication type
Article
Status
Published
Authors
M. V. Kozlova
  • Affiliation: I.N. Ulyanov Chuvash State University
I. N Bardasov
  • Affiliation: I.N. Ulyanov Chuvash State University
Volume/ Edition
Volume 93 / Issue number 8
Pages
1206-1215
Abstract
The reaction of 4-amino-6-aryl-2-halopyridine-3,5-dicarbonitriles with thioglycolic acid ethyl ester was used to synthesize a series of new efficient fluorophores of thieno[2,3- b ]pyridine series. The long-wavelength absorption bands of DMSO solutions of the prepared compounds are at the boundary of the UV and visible regions of the spectrum (λabs 375-388 nm) and show an ambiguous influence of the substituent electronic effect, that was explained by quantum chemical calculations. The emission maxima are in the yellow-green region (λem 490- 510 nm) and they are blue-shifted in the presence of electron donor groups with slightly increasing intensity (Φem 37.8-60.6%). It was found that the nitro group presence causes a complete photoluminescence quenching both in solution and in the solid state. In addition, the position of the emission maximum (λem 473-505 nm) and its intensity (Φem 3.6-72.7%) strongly depend on the polarity and the basic properties of the medium, that was established using the Catalan empirical model.
Keywords
тиено[2,3-b]пиридины флуоресценция сольватохромизм нуклеофильное замещение
Date of publication
17.09.2025
Year of publication
2025
Number of purchasers
0
Views
13

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