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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| Published in | Beilstein journal of organic chemistry Vol. 13; no. 1; pp. 313 - 322 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
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Beilstein-Institut zur Föerderung der Chemischen Wissenschaften
17.02.2017
Beilstein-Institut |
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| 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 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. |
|---|---|
| AbstractList | 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.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. 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 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. 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. 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. |
| Author | Zheleznova, Tatyana Yu Stasyuk, Anton Jaroslavovich Kostyuchenko, Anastasia Sergeevna Pron, Adam Domagala, Wojciech Kurowska, Aleksandra Fisyuk, Alexander S |
| AuthorAffiliation | 3 Department of Chemistry and RECETOX, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic 5 Faculty of Chemistry , Warsaw University of Technology, Noakowskiego 3, 00-664 Warszawa, Poland 2 Department of Organic Chemistry, Faculty of Science, RUDN University, 6 Miklukho-Maklaya st., 117198 Moscow, Russian Federation 1 Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave, 11, 644050 Omsk, Russian Federation 6 Department of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira pr., 644077 Omsk, Russian Federation 4 Department of Physical Chemistry and Technology of Polymers, Silesian University of Technology, Marcina Strzody 9, 44-100 Gliwice, Poland |
| AuthorAffiliation_xml | – name: 5 Faculty of Chemistry , Warsaw University of Technology, Noakowskiego 3, 00-664 Warszawa, Poland – name: 6 Department of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira pr., 644077 Omsk, Russian Federation – name: 2 Department of Organic Chemistry, Faculty of Science, RUDN University, 6 Miklukho-Maklaya st., 117198 Moscow, Russian Federation – name: 4 Department of Physical Chemistry and Technology of Polymers, Silesian University of Technology, Marcina Strzody 9, 44-100 Gliwice, Poland – name: 3 Department of Chemistry and RECETOX, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic – name: 1 Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave, 11, 644050 Omsk, Russian Federation |
| Author_xml | – sequence: 1 givenname: Anastasia Sergeevna surname: Kostyuchenko fullname: Kostyuchenko, Anastasia Sergeevna – sequence: 2 givenname: Tatyana Yu surname: Zheleznova fullname: Zheleznova, Tatyana Yu – sequence: 3 givenname: Anton Jaroslavovich surname: Stasyuk fullname: Stasyuk, Anton Jaroslavovich – sequence: 4 givenname: Aleksandra surname: Kurowska fullname: Kurowska, Aleksandra – sequence: 5 givenname: Wojciech surname: Domagala fullname: Domagala, Wojciech – sequence: 6 givenname: Adam surname: Pron fullname: Pron, Adam – sequence: 7 givenname: Alexander S surname: Fisyuk fullname: Fisyuk, Alexander S |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28326140$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/cm051563i 10.1016/j.electacta.2013.07.209 10.3762/bjoc.10.165 10.1039/B417642A 10.1002/ejoc.200900964 10.1039/C5RA06811H 10.1021/jp507838c 10.1039/b907999h 10.1039/b922714h 10.1021/ol500356w 10.1021/jp047289h 10.1007/s10853-015-9529-4 10.1039/c1cp22144b 10.1002/chem.201600984 10.1002/(SICI)1521-3765(19981102)4:11<2211::AID-CHEM2211>3.0.CO;2-7 10.1039/b415587d 10.1016/S0040-4039(97)10395-1 10.1039/c2cs35394f 10.1021/cm802937x 10.1016/j.optmat.2014.05.023 10.1039/c3cs60257e 10.1021/ja807219x 10.1016/j.tet.2004.06.075 10.1021/cr8004229 10.1002/(SICI)1099-0690(200002)2000:3<425::AID-EJOC425>3.0.CO;2-Z 10.1021/cr900357e 10.1021/cm201424a 10.1039/B606320A 10.1021/cr100380z 10.1071/CH12171 10.1021/jp401448a 10.1021/la4034707 |
| ContentType | Journal Article |
| Copyright | Copyright © 2017, Kostyuchenko et al.; licensee Beilstein-Institut. This work is licensed under the Creative Commons Attribution License (https://creativecommons.org/licenses/by/3.0/) (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. Copyright © 2017, Kostyuchenko et al. 2017 Kostyuchenko et al. |
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| Keywords | donor–acceptor bithiophene palladium-catalyzed coupling luminescence 1,3,4-oxadiazole |
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| Snippet | 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... 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... |
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| SubjectTerms | 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 |
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| Title | Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/28326140 https://www.proquest.com/docview/1953040718 https://www.proquest.com/docview/1880086483 https://pubmed.ncbi.nlm.nih.gov/PMC5331275 https://doaj.org/article/09bbdb1f99d641beb6573d356d25de61 |
| Volume | 13 |
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