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The effect of electron-donating moiety structure on the electrochemical and photophysical properties of dithiophene- and naphtho[2,1-b:3,4-b']dithiophene-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles

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Chemistry of Heterocyclic Compounds Aims and scope

3-Alkyl- and 3-aryl-substituted [2,2'-dithiophene]-5-carboxylate esters, as well as naphtho[2,1-b:3,4-b']dithiophene-2-carboxylates were used in the synthesis of 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives. The obtained compounds were characterized with regard to their electrochemical and photophysical properties. The replacement of alkyl side chains with aryl substituents led to a substantial decrease of luminescence quantum yield and narrowing the energy gap between HOMO and LUMO, as well as a bathochromic shift of the absorption and emission peaks in the absorption and luminescence spectra. Changing from 3-aryldithiophene- to naphtho[2,1-b:3,4-b']-dithiophene-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles led to a slight increase of quantum yields, while the positions of LUMO and HOMO changed insignificantly.

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Correspondence to Alexander S. Fisyuk.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(1/2), 88–95

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Uliankin, E.B., Kostyuchenko, A.S. & Fisyuk, A.S. The effect of electron-donating moiety structure on the electrochemical and photophysical properties of dithiophene- and naphtho[2,1-b:3,4-b']dithiophene-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles. Chem Heterocycl Comp 59, 88–95 (2023). https://doi.org/10.1007/s10593-023-03166-2

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