Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles.
New photoluminescent donor-acceptor-donor (DAD) molecules, namely 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles were prepared by palladium-catalyzed coupling from readily available compounds such as ethyl 3-decyl-2,2'-bithiophene-5-carboxylate and aryl halides. The obtained compounds feature increasing bathochromic shifts in their emission spectra with increasing aryl-substituent size yielding blue to bluish-green emissions. At the same time, their absorption spectra are almost independent from the identity of the terminal substituent with λmaxvalues ranging from 395 to 405 nm. The observed trends are perfectly predicted by quantum chemical DFT/TDDFT calculations carried out for these new molecules.
Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave, 11, 644050 Omsk, Russian Federation; Department of Organic Chemistry, Faculty of Science, RUDN University, 6 Miklukho-Maklaya st., 117198 Moscow, Russian Federation.
Anastasia Sergeevna
AS
Kostyuchenko
Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave, 11, 644050 Omsk, Russian Federation.
Tatyana Yu
TY
Zheleznova
Department of Chemistry and RECETOX, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic.
Anton Jaroslavovich
AJ
Stasyuk
Department of Physical Chemistry and Technology of Polymers, Silesian University of Technology, Marcina Strzody 9, 44-100 Gliwice, Poland.
Aleksandra
A
Kurowska
Department of Physical Chemistry and Technology of Polymers, Silesian University of Technology, Marcina Strzody 9, 44-100 Gliwice, Poland.
Wojciech
W
Domagala
Faculty of Chemistry , Warsaw University of Technology, Noakowskiego 3, 00-664 Warszawa, Poland.
Adam
A
Pron
Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave, 11, 644050 Omsk, Russian Federation; Department of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira pr., 644077 Omsk, Russian Federation.
Alexander S
AS
Fisyuk
1,3,4-oxadiazole; bithiophene; donor–acceptor; luminescence; palladium-catalyzed coupling