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Synthesis and Optical Properties of New 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles

Synthesis and Optical Properties of New 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles

Anastasia Sergeevna Kostyuchenko, Tatyana Yu Zheleznova, Anton Jaroslavovich Stasyuk, Aleksandra Kurowska, Wojciech Domagala, Adam Pron, Alexander S Fisyuk

Beilstein J Org Chem. 2017 Feb 17;13:313-322.

PMID: 28326140

Abstract:

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 λmax 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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP125143535	3,3′,5,5′-Tetrabromo-2,2′-bithiophene		125143-53-5	Price
AP327630342	5-Perfluorohexyl-2,2′-bithiophene		327630-34-2	Price

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