Higly Luminescent Aceno[6]helicenones by Intramolecular Radical Cyclization - Archive ouverte HAL
Article Dans Une Revue Chemistry - A European Journal Année : 2024

Higly Luminescent Aceno[6]helicenones by Intramolecular Radical Cyclization

Résumé

Helicenes and helicenoid structures are promising candidates for future applications exploiting circularly polarized light. Ideal candidates should possess near‐quantitative photoluminescence quantum yield, high a luminescence dissymmetry factor and an adjustable HOMO‐LUMO gap. However, carbo[n]helicenes are poorly luminescent compounds and they absorb light mainly in the ultraviolet region. Here we show that the incorporation of a carbonyl group into helical scaffold significantly improves the fluorescence quantum yield and shifts the absorption to visible region. Although the carbonyl group is commonly considered as detrimental to efficient emission, fluorescence quantum yields up to Φ = 0.43 were recorded. A straightforward synthetic approach to a highly luminescent tetraceno[6]helicenone and an aza analogue has been developed. The key step is a radical cyclization which is achieving dehydrative π‐extension. The aza‐analogue was incorporated as an emitter in organic light emitting diodes (OLEDs) and showed good performance.

Domaines

Chimie
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Dates et versions

hal-04778248 , version 1 (11-12-2024)

Identifiants

Citer

Ludmilla Sturm, Marzena Banasiewicz, Irena Deperasinska, Boleslaw Kozankiewicz, Olaf Morawski, et al.. Higly Luminescent Aceno[6]helicenones by Intramolecular Radical Cyclization. Chemistry - A European Journal, 2024, 30 (72), pp.e202403482. ⟨10.1002/chem.202403482⟩. ⟨hal-04778248⟩
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