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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2017
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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. |
format | Online Article Text |
id | pubmed-5331275 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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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