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Abstract
An air-stable B3,N3-containing dibenzobisanthene (8) was prepared in 29% yield by heating a 1,3,5-tri(azasilaanthryl)benzene (5) with BBr3 (180 °C). Under these conditions, the reaction does not stop after threefold SiMe2/BBr exchange but proceeds further via two rearrangement and two intramolecular C-H borylation steps. Some mechanistic details were unveiled by using smaller model systems and applying lower reaction temperatures. According to X-ray crystallography, compound 8 has a helically distorted scaffold. Due to its multiple resonance structure, it shows a narrow-band blue-green emission (λem = 493 nm; ΦPL = 84%; FWHM = 0.20 eV; THF); samples measured in PMMA gave prompt and delayed fluorescence lifetimes of 10.7 ns and 136 μs, respectively. The optical properties of 8 and of structurally related species were also investigated by quantum-chemical means: most of these compounds exhibit a small energy gap ΔEST between the lowest excited singlet (S1) and triplet (T1) states and a non-negligible spin-orbit coupling (SOC) between S1 and T1/T2, demonstrating their potential as thermally activated delayed fluorescence (TADF) emitters.
Original language | English |
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Pages (from-to) | 9294-9300 |
Number of pages | 7 |
Journal | Dalton Transactions |
Volume | 53 |
Issue number | 22 |
DOIs | |
Publication status | Published - 8 May 2024 |
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Dive into the research topics of 'Borylation and rearrangement reactions of azasilaanthracenes to afford B,N-doped nanographenes'. Together they form a unique fingerprint.Projects
- 1 Finished
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Equipment renewal for the Consortium des Equipements de Calcul Intensif (CECI)
Bontempi, G. (PI), CHAMPAGNE, B. (CoPI), Geuzaine , C. (CoPI), RIGNANESE, G. M. (CoPI) & Lazzaroni, R. (CoPI)
1/01/22 → 31/12/23
Project: Research
Equipment
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High Performance Computing Technology Platform
Champagne, B. (Manager)
Technological Platform High Performance ComputingFacility/equipment: Technological Platform