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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

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 ha...

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Autores principales: Kostyuchenko, Anastasia Sergeevna, Zheleznova, Tatyana Yu, Stasyuk, Anton Jaroslavovich, Kurowska, Aleksandra, Domagala, Wojciech, Pron, Adam, Fisyuk, Alexander S
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5331275/
https://www.ncbi.nlm.nih.gov/pubmed/28326140
http://dx.doi.org/10.3762/bjoc.13.34
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author Kostyuchenko, Anastasia Sergeevna
Zheleznova, Tatyana Yu
Stasyuk, Anton Jaroslavovich
Kurowska, Aleksandra
Domagala, Wojciech
Pron, Adam
Fisyuk, Alexander S
author_facet Kostyuchenko, Anastasia Sergeevna
Zheleznova, Tatyana Yu
Stasyuk, Anton Jaroslavovich
Kurowska, Aleksandra
Domagala, Wojciech
Pron, Adam
Fisyuk, Alexander S
author_sort Kostyuchenko, Anastasia Sergeevna
collection PubMed
description 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.
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spelling pubmed-53312752017-03-21 Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles Kostyuchenko, Anastasia Sergeevna Zheleznova, Tatyana Yu Stasyuk, Anton Jaroslavovich Kurowska, Aleksandra Domagala, Wojciech Pron, Adam Fisyuk, Alexander S Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2017-02-17 /pmc/articles/PMC5331275/ /pubmed/28326140 http://dx.doi.org/10.3762/bjoc.13.34 Text en Copyright © 2017, Kostyuchenko et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Kostyuchenko, Anastasia Sergeevna
Zheleznova, Tatyana Yu
Stasyuk, Anton Jaroslavovich
Kurowska, Aleksandra
Domagala, Wojciech
Pron, Adam
Fisyuk, Alexander S
Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles
title Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles
title_full Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles
title_fullStr Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles
title_full_unstemmed Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles
title_short Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles
title_sort synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5331275/
https://www.ncbi.nlm.nih.gov/pubmed/28326140
http://dx.doi.org/10.3762/bjoc.13.34
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