Highly Luminescent Aceno[6]helicenones by Intramolecular Radical Cyclization
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F24%3A00603245" target="_blank" >RIV/61388963:_____/24:00603245 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1002/chem.202403482" target="_blank" >https://doi.org/10.1002/chem.202403482</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.202403482" target="_blank" >10.1002/chem.202403482</a>
Alternative languages
Result language
angličtina
Original language name
Highly Luminescent Aceno[6]helicenones by Intramolecular Radical Cyclization
Original language description
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 Phi=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 pi-extension. The aza-analogue was incorporated as an emitter in organic light emitting diodes (OLEDs) and showed good performance.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GA20-23566S" target="_blank" >GA20-23566S: The synthesis and properties of polycyclic inherently chiral aromatics</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemistry - A European Journal
ISSN
0947-6539
e-ISSN
1521-3765
Volume of the periodical
30
Issue of the periodical within the volume
72
Country of publishing house
DE - GERMANY
Number of pages
6
Pages from-to
e202403482
UT code for WoS article
001364584500001
EID of the result in the Scopus database
2-s2.0-85210505508