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

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 °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 °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.

New Advances in π-Conjugated Materials

“…Skhirtladze synthesized two molecules by Buchwald–Hartwig coupling reactions with pyridazine as the electrophoretic core and 9,9-dimethyl-9,10-dihydroacridine or phenoxazine as the donor, which were called 2PO-PYD and 2AC-PYD, respectively [ 3 ]. They have high photoluminescence quantum efficiency, and the gap between the first excited singlet state (S1) to the first excited triplet state (T1) is small; this can contribute to efficient transfer from S1 to T1 by thermally activated delayed fluorescence (TADF).…”