THE EFFECT OF ELECTRON-DONATING MOIETY STRUCTURE ON THE ELECTROCHEMICAL AND PHOTOPHYSICAL PROPERTIES OF DITHIOPHENE- AND NAPHTHO[2,1-<i>b</i>:3,4-<i>b</i>']DITHIOPHENE-SUBSTITUTED 1,3,4-OXADIAZOLES AND 1,3,4-THIADIAZOLES

Authors

  • Евгений Б. Ульянкин Dostoevsky Omsk State University, 55а Mira Ave., Omsk 644077, Russia Omsk State Technical University, 11 Mira Ave., Omsk 644050, Russia
  • Анастасия С. Костюченко Dostoevsky Omsk State University, 55а Mira Ave., Omsk 644077, Russia Omsk State Technical University, 11 Mira Ave., Omsk 644050, Russia
  • Александр С. Фисюк Dostoevsky Omsk State University, 55а Mira Ave., Omsk 644077, Russia Omsk State Technical University, 11 Mira Ave., Omsk 644050, Russia

DOI:

https://doi.org/10.1007/7127

Keywords:

2, 2'-dithiophenes, naphtho[2, 1-b, 3, 4-b']dithiophenes, 1, 4-oxadiazoles, 4-thiadiazoles, luminophores, organic electronics.

Abstract

3-Alkyl- and 3-aryl-substituted [2,2'-dithiophene]-5-carboxylate esters, as well as naphtho[2,1-b:3,4-b']dithiophene-2carboxylates 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 3aryldithiophene- 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.

 

Author Biography

Евгений Б. Ульянкин, Dostoevsky Omsk State University, 55а Mira Ave., Omsk 644077, Russia Omsk State Technical University, 11 Mira Ave., Omsk 644050, Russia

Заведующий кафедрой органической химии ОмГУ им. Ф.М. Достоевского, заведующий лабораторией "Новые органические материалы" ОмГТУ, д.х.н., профессор.

Published

2023-02-21

Issue

Section

Original Papers