Carbonyl mediated fluorescence in aceno[n]helicenones and fluoreno[n]helicenes

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F24%3A00586800" target="_blank" >RIV/61388963:_____/24:00586800 - isvavai.cz</a>

Výsledek na webu

<a href="https://doi.org/10.1039/D4SC00892H" target="_blank" >https://doi.org/10.1039/D4SC00892H</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d4sc00892h" target="_blank" >10.1039/d4sc00892h</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Carbonyl mediated fluorescence in aceno[n]helicenones and fluoreno[n]helicenes

Popis výsledku v původním jazyce

Helicenes are very attractive chiral non-planar polycyclic aromatic hydrocarbons possessing strong chiroptical properties. However, most of the helicenes absorb light mainly in the ultraviolet region, with only a small segment in the blue part of the visible spectrum. Furthermore, carbo[n]helicenes exhibit only weak luminescence that limits their utilization. Herein, we demonstrate that peripheral decoration of the helicene backbone with an aryl-carbonyl group shifts the absorption to the visible region and simultaneously improves their fluorescence quantum yields. We thus show that the carbonyl group, commonly considered as detrimental to emission, has the capability of improving optical and photophysical properties. Two different families, aceno[n]helicenones and fluoreno[n]helicenes, are presented with comprehensive spectrochemical characterization. TD-DFT calculations were implemented to clarify their electronic profiles. We show that increasing the helical length in aceno[n]helicenes increases absorption onset, g(abs) and g(lum). Extension of the peripheral aromatic part in fluoreno[n]helicenes leads to a blue shift in both absorption and emission.

Název v anglickém jazyce

Carbonyl mediated fluorescence in aceno[n]helicenones and fluoreno[n]helicenes

Popis výsledku anglicky

Helicenes are very attractive chiral non-planar polycyclic aromatic hydrocarbons possessing strong chiroptical properties. However, most of the helicenes absorb light mainly in the ultraviolet region, with only a small segment in the blue part of the visible spectrum. Furthermore, carbo[n]helicenes exhibit only weak luminescence that limits their utilization. Herein, we demonstrate that peripheral decoration of the helicene backbone with an aryl-carbonyl group shifts the absorption to the visible region and simultaneously improves their fluorescence quantum yields. We thus show that the carbonyl group, commonly considered as detrimental to emission, has the capability of improving optical and photophysical properties. Two different families, aceno[n]helicenones and fluoreno[n]helicenes, are presented with comprehensive spectrochemical characterization. TD-DFT calculations were implemented to clarify their electronic profiles. We show that increasing the helical length in aceno[n]helicenes increases absorption onset, g(abs) and g(lum). Extension of the peripheral aromatic part in fluoreno[n]helicenes leads to a blue shift in both absorption and emission.

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

Chemical Science

ISSN

2041-6520

e-ISSN

2041-6539

Svazek periodika

15

Číslo periodika v rámci svazku

25

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

9842-9850

Kód UT WoS článku

001234393800001

EID výsledku v databázi Scopus

2-s2.0-85194384925