Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles

• Published in: Beilstein journal of organic chemistry Vol. 13; no. 1; pp. 313 - 322
• Main Authors: Kostyuchenko, Anastasia Sergeevna, Zheleznova, Tatyana Yu, Stasyuk, Anton Jaroslavovich, Kurowska, Aleksandra, Domagala, Wojciech, Pron, Adam, Fisyuk, Alexander S
• Format: Journal Article
• Language: English
• Published: Germany Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 17.02.2017; Beilstein-Institut
• Subjects: 1,3,4-oxadiazole; Acids; bithiophene; Chemistry; Chromatography; donor–acceptor; Emissions; Full Research Paper; luminescence; Optical properties; Organic light emitting diodes; Palladium; palladium-catalyzed coupling; donor–acceptor; bithiophene; palladium-catalyzed coupling; luminescence; 1,3,4-oxadiazole
• ISSN: 1860-5397; 2195-951X; 1860-5397
• DOI: 10.3762/bjoc.13.34

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 λ max values ranging from 395 to 405 nm. The observed trends are perfectly predicted by quantum chemical DFT/TDDFT calculations carried out for these new molecules.