Highly Luminescent Aceno[6]helicenones by Intramolecular Radical Cyclization
Helicenes and helicenoid structures are promising candidates for future applications exploiting circularly polarized light. Ideal candidates should possess near-quantitative photoluminescence quantum yield, a high 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.
Authors
- Michal Šámal (ORCID: https://orcid.org/0000-0002-1395-4917)
- Irena Deperasińska (ORCID: https://orcid.org/0000-0002-1680-9504)
- Β. Kozankiewicz (ORCID: https://orcid.org/0000-0002-2507-2356)
- Yuuya Nagata (ORCID: https://orcid.org/0000-0001-5926-5845)
- Ludmilla Sturm (ORCID: https://orcid.org/0009-0007-4497-4578)
- Isabelle Séguy (ORCID: https://orcid.org/0000-0002-7788-4823)
- Pierre Dechambenoit (ORCID: https://orcid.org/0000-0001-7850-2260)
- Ludovic Salvagnac (ORCID: https://orcid.org/0000-0001-8862-5889)
- Marzena Banasiewicz (ORCID: https://orcid.org/0000-0002-8251-5440)
- Andrej Jančařík (ORCID: https://orcid.org/0000-0002-6944-1002)
- Harald Böck (ORCID: https://orcid.org/0000-0002-0479-8203)
- Olaf Morawski (ORCID: https://orcid.org/0000-0002-9475-668X)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Université Toulouse III - Paul Sabatier (FR)
- Université de Bordeaux (FR)
- Université Fédérale de Toulouse Midi-Pyrénées (FR)
- Laboratoire d'Analyse et d'Architecture des Systèmes (FR)
- Hokkaido University (JP)
- Institute of Physics (PL)
- Centre National pour la Recherche Scientifique et Technique (CNRST) (MA)
- Institute of Organic Chemistry (PL)
- FZU ‒ Institute of Physics of the Academy of Sciences of the Czech Republic (CZ)
- Japan Research Institute (JP)
- Center for Research in Psychopathology and Clinical Psychology (FR)
- Centre de recherche Paul Pascal (FR)
- Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry (CZ)
- Polish Academy of Sciences (PL)
Publication Details
- Journal
- Chemistry - A European Journal
- Published
- 2024-10-16
- DOI
- https://doi.org/10.1002/chem.202403482
- Citations
- 1
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- Ministry of Education, Culture, Sports, Science and Technology
- Grantová Agentura České Republiky
- Akademie Věd České Republiky
- Centre National de la Recherche Scientifique
- Université de Bordeaux
- Uniwersytet Warszawski
- Japan Society for the Promotion of Science
- Ústav organické chemie a biochemie Akademie věd České republiky
- Core Research for Evolutional Science and Technology
- Exploratory Research for Advanced Technology