Open Access Open Access  Restricted Access Subscription Access

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

Евгений Б. Ульянкин, Анастасия С. Костюченко, Александр С. Фисюк
Cover Image

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.

 


Keywords


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

Full Text: PDF (Russian) Supplementary File(s): Supplementary information (1MB)


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv