Derivatives of Pyridazine with Phenoxazine and 9,9-Dimethyl-9,10-dihydroacridine Donor Moieties Exhibiting Thermally Activated Delayed Fluorescence

Skhirtladze, Levani and Bezvikonnyi, Oleksandr and Keruckiene, Rasa and Dvylys, Lukas and Mahmoudi, Malek and Labanauskas, Linas and Ariffin, Azhar and Grazulevicius, Juozas V. V. (2023) Derivatives of Pyridazine with Phenoxazine and 9,9-Dimethyl-9,10-dihydroacridine Donor Moieties Exhibiting Thermally Activated Delayed Fluorescence. Materials, 16 (3). ISSN 1996-1944, DOI https://doi.org/10.3390/ma16031294.

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Abstract

Two compounds based on pyridazine as the acceptor core and 9,9-dimethyl-9,10-dihydroacridine or phenoxazine donor moieties were designed and synthesized by Buchwald-Hartwig cross-coupling reaction. The electronic, photophysical, and electrochemical properties of the compounds were studied by ultraviolet-visible spectroscopy (UV-vis), photoluminescence spectrometry, differential scanning calorimetry, thermogravimetric analysis, and cyclic voltammetry. The compounds are characterized by high thermal stabilities. Their 5% weight loss temperatures are 314 and 336 degrees C. Complete weight loss of both pyridazine-based compounds was detected by TGA, indicating sublimation. The derivative of pyridazine and 9,9-dimethyl-9,10-dihydroacridine is capable of glass formation. Its glass transition temperature is 80 degrees C. The geometries and electronic characteristics of the compounds were substantiated using density functional theory (DFT). The compounds exhibited emission from the intramolecular charge transfer state manifested by positive solvatochromism. The emission in the range of 534-609 nm of the toluene solutions of the compounds is thermally activated delayed fluorescence with lifetimes of 93 and 143 ns, respectively.

Item Type: Article
Funders: European Union (EU) (823720), Marie Curie Actions (823720)
Uncontrolled Keywords: pyridazine; 9; 9-dimethyl-9; 10-dihydroacridine; phenoxazine; delayed fluorescence
Subjects: Q Science > QC Physics
Q Science > QD Chemistry
T Technology > T Technology (General)
Depositing User: Ms Zaharah Ramly
Date Deposited: 23 Nov 2023 07:21
Last Modified: 23 Nov 2023 07:21
URI: http://eprints.um.edu.my/id/eprint/38738

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