Highly Luminescent Aceno[6]helicenones by Intramolecular Radical Cyclization

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Highly Luminescent Aceno[6]helicenones by Intramolecular Radical Cyclization

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Highly Luminescent Aceno[6]helicenones by Intramolecular Radical Cyclization

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA20-23566S" target="_blank" >GA20-23566S: Syntéza a vlastnosti polycyklických inherentně chirálních aromátů</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Chemistry - A European Journal

ISSN

0947-6539

e-ISSN

1521-3765

Svazek periodika

30

Číslo periodika v rámci svazku

72

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

6

Strana od-do

e202403482

Kód UT WoS článku

001364584500001

EID výsledku v databázi Scopus

2-s2.0-85210505508