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

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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.

About the authors

A. U Alekseeva

I.N. Ulyanov Chuvash State University

M. Yu. Ievlev

I.N. Ulyanov Chuvash State University

E. G Zinovieva

I.N. Ulyanov Chuvash State University

O. V Ershov

I.N. Ulyanov Chuvash State University

A. I Ershova

I.N. Ulyanov Chuvash State University

I. N Bardasov

I.N. Ulyanov Chuvash State University

Email: bardasov.chem@mail.ru

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