Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions
The pyridine-3,5-dicarbonitrile moiety has gained significant attention in the field of materials chemistry, particularly in the development of heavy-metal-free pure organic light-emitting diodes (OLEDs). Extensive research on organic compounds exhibiting thermally activated delayed fluorescence (TA...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2023-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.19.139 |
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| author | Karolis Leitonas Brigita Vigante Dmytro Volyniuk Audrius Bucinskas Pavels Dimitrijevs Sindija Lapcinska Pavel Arsenyan Juozas Vidas Grazulevicius |
| author_facet | Karolis Leitonas Brigita Vigante Dmytro Volyniuk Audrius Bucinskas Pavels Dimitrijevs Sindija Lapcinska Pavel Arsenyan Juozas Vidas Grazulevicius |
| author_sort | Karolis Leitonas |
| collection | DOAJ |
| description | The pyridine-3,5-dicarbonitrile moiety has gained significant attention in the field of materials chemistry, particularly in the development of heavy-metal-free pure organic light-emitting diodes (OLEDs). Extensive research on organic compounds exhibiting thermally activated delayed fluorescence (TADF) has led to numerous patents and research articles. This study focuses on the synthesis and investigation of the semiconducting properties of polyaromatic π-systems containing two and three fragments of pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile. The compounds are synthesized by Sonogashira coupling reactions and characterized by steady-state and time-resolved luminescence spectroscopy. The compounds show efficient intramolecular charge transfer (ICT) from the donor to the acceptor. The photoluminescence (PL) spectra of the solutions of the compounds showed non-structured emission peaks in the visible region, which are attributed to ICT emission. The PL intensities of the solutions of the compounds are enhanced after deoxygenation, which is indicative of TADF. The photoluminescence quantum yields and TADF properties of the compounds are sensitive to the medium. Cyclic voltammetry measurements indicate good hole-blocking and electron-injecting properties due to their high ionization potentials. Photoelectron spectroscopy and time-of-flight measurements reveal good electron-transporting properties for one of the compounds. In general, polyaromatic π-systems with pyridine-3,5-dicarbonitrile fragments demonstrate promising potential for use in organic electronic devices, such as OLEDs. |
| first_indexed | 2024-03-08T05:29:18Z |
| format | Article |
| id | doaj.art-c41dca9c3ce64667a7b343bb7cddd070 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-03-08T05:29:18Z |
| publishDate | 2023-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-c41dca9c3ce64667a7b343bb7cddd0702024-02-06T09:08:29ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972023-12-011911867188010.3762/bjoc.19.1391860-5397-19-139Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissionsKarolis Leitonas0Brigita Vigante1Dmytro Volyniuk2Audrius Bucinskas3Pavels Dimitrijevs4Sindija Lapcinska5Pavel Arsenyan6Juozas Vidas Grazulevicius7Department of Polymer Chemistry and Technology, Kaunas University of Technology, Radvilenu pl. 19, LT-50254, Kaunas, Lithuania Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia Department of Polymer Chemistry and Technology, Kaunas University of Technology, Radvilenu pl. 19, LT-50254, Kaunas, Lithuania Department of Polymer Chemistry and Technology, Kaunas University of Technology, Radvilenu pl. 19, LT-50254, Kaunas, Lithuania Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia Department of Polymer Chemistry and Technology, Kaunas University of Technology, Radvilenu pl. 19, LT-50254, Kaunas, Lithuania The pyridine-3,5-dicarbonitrile moiety has gained significant attention in the field of materials chemistry, particularly in the development of heavy-metal-free pure organic light-emitting diodes (OLEDs). Extensive research on organic compounds exhibiting thermally activated delayed fluorescence (TADF) has led to numerous patents and research articles. This study focuses on the synthesis and investigation of the semiconducting properties of polyaromatic π-systems containing two and three fragments of pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile. The compounds are synthesized by Sonogashira coupling reactions and characterized by steady-state and time-resolved luminescence spectroscopy. The compounds show efficient intramolecular charge transfer (ICT) from the donor to the acceptor. The photoluminescence (PL) spectra of the solutions of the compounds showed non-structured emission peaks in the visible region, which are attributed to ICT emission. The PL intensities of the solutions of the compounds are enhanced after deoxygenation, which is indicative of TADF. The photoluminescence quantum yields and TADF properties of the compounds are sensitive to the medium. Cyclic voltammetry measurements indicate good hole-blocking and electron-injecting properties due to their high ionization potentials. Photoelectron spectroscopy and time-of-flight measurements reveal good electron-transporting properties for one of the compounds. In general, polyaromatic π-systems with pyridine-3,5-dicarbonitrile fragments demonstrate promising potential for use in organic electronic devices, such as OLEDs.https://doi.org/10.3762/bjoc.19.139charge transportintramolecular charge transferphotophysical propertiespyridine-3,5-dicarbonitrile |
| spellingShingle | Karolis Leitonas Brigita Vigante Dmytro Volyniuk Audrius Bucinskas Pavels Dimitrijevs Sindija Lapcinska Pavel Arsenyan Juozas Vidas Grazulevicius Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions Beilstein Journal of Organic Chemistry charge transport intramolecular charge transfer photophysical properties pyridine-3,5-dicarbonitrile |
| title | Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions |
| title_full | Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions |
| title_fullStr | Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions |
| title_full_unstemmed | Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions |
| title_short | Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions |
| title_sort | aromatic systems with two and three pyridine 2 6 dicarbazolyl 3 5 dicarbonitrile fragments as electron transporting organic semiconductors exhibiting long lived emissions |
| topic | charge transport intramolecular charge transfer photophysical properties pyridine-3,5-dicarbonitrile |
| url | https://doi.org/10.3762/bjoc.19.139 |
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