Effect of the substituent position on the electrochemical, optical and structural properties of donor-acceptor type acridone derivatives

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389013%3A_____%2F20%3A00524240" target="_blank" >RIV/61389013:_____/20:00524240 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlelanding/2020/CP/D0CP00521E#!divAbstract" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2020/CP/D0CP00521E#!divAbstract</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/D0CP00521E" target="_blank" >10.1039/D0CP00521E</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Effect of the substituent position on the electrochemical, optical and structural properties of donor-acceptor type acridone derivatives

Popis výsledku v původním jazyce

Three new donor–acceptor (D–A) compounds, positional isomers of phenoxazine-substituted acridone, namely 1-phenoxazine-N-hexylacridone (o-A), 2-phenoxazine-N-hexylacridone (m-A) and 3-phenoxazine-N-hexylacridone (p-A), were synthesized. The synthesized compounds showed interesting, isomerism-dependent electrochemistry. Their oxidation was reversible and their potential (given vs. Fc/Fc+) changed from 0.21 V for o-A to 0.36 V for p-A. In contrast, their reduction was irreversible, isomerism-independent and occurred at rather low potentials (ca. −2.25 to −2.28 V). The electrochemical results led to the following values of the ionization potentials (IPs) and electron affinities (EAs): 5.03 eV and −2.14 eV, 5.15 eV and −2.20 eV, and 5.20 eV and −2.28 eV for o-A, m-A and p-A, respectively. The experimentally obtained values were in very good agreement with those predicted by DFT calculations. All three isomers readily formed single crystals suitable for their structure determination. o-A and p-A crystallized in P[1 with combining macron] and P21/n space groups, respectively, with one molecule per asymmetric unit, while m-A crystallized in the P21/c space group with two molecules in the asymmetric unit accompanied by disordered solvent molecules. The UV-vis spectra of the studied compounds were isomerism and solvent independent, yielding absorption maxima in the vicinity of 400 nm. Their photoluminescence spectra, in turn, strongly depended on isomerism and the used solvent showing smaller Stokes shifts for the emission bands registered in toluene as compared to the corresponding bands measured in dichloromethane. The photoluminescence quantum yields (ϕ) were systematically higher for toluene solutions reaching the highest value of 20% for p-A. For all three isomers studied, stationary and time-resolved spectroscopic investigations carried out in toluene at different temperatures revealed spectral features indicating a contribution of thermally activated delayed fluorescence (TADF) to the observed spectroscopic behaviour. The measured photoluminescence quantum yields (ϕ) were higher for solid state films of pure compounds and for their dispersions in solid matrices (zeonex) than those recorded for toluene and dichloromethane solutions of the studied phenoxazine-N-hexylacridone isomers. The obtained experimental spectroscopic and structural data were confronted with theoretical predictions based on DFT calculations.

Název v anglickém jazyce

Effect of the substituent position on the electrochemical, optical and structural properties of donor-acceptor type acridone derivatives

Popis výsledku anglicky

Three new donor–acceptor (D–A) compounds, positional isomers of phenoxazine-substituted acridone, namely 1-phenoxazine-N-hexylacridone (o-A), 2-phenoxazine-N-hexylacridone (m-A) and 3-phenoxazine-N-hexylacridone (p-A), were synthesized. The synthesized compounds showed interesting, isomerism-dependent electrochemistry. Their oxidation was reversible and their potential (given vs. Fc/Fc+) changed from 0.21 V for o-A to 0.36 V for p-A. In contrast, their reduction was irreversible, isomerism-independent and occurred at rather low potentials (ca. −2.25 to −2.28 V). The electrochemical results led to the following values of the ionization potentials (IPs) and electron affinities (EAs): 5.03 eV and −2.14 eV, 5.15 eV and −2.20 eV, and 5.20 eV and −2.28 eV for o-A, m-A and p-A, respectively. The experimentally obtained values were in very good agreement with those predicted by DFT calculations. All three isomers readily formed single crystals suitable for their structure determination. o-A and p-A crystallized in P[1 with combining macron] and P21/n space groups, respectively, with one molecule per asymmetric unit, while m-A crystallized in the P21/c space group with two molecules in the asymmetric unit accompanied by disordered solvent molecules. The UV-vis spectra of the studied compounds were isomerism and solvent independent, yielding absorption maxima in the vicinity of 400 nm. Their photoluminescence spectra, in turn, strongly depended on isomerism and the used solvent showing smaller Stokes shifts for the emission bands registered in toluene as compared to the corresponding bands measured in dichloromethane. The photoluminescence quantum yields (ϕ) were systematically higher for toluene solutions reaching the highest value of 20% for p-A. For all three isomers studied, stationary and time-resolved spectroscopic investigations carried out in toluene at different temperatures revealed spectral features indicating a contribution of thermally activated delayed fluorescence (TADF) to the observed spectroscopic behaviour. The measured photoluminescence quantum yields (ϕ) were higher for solid state films of pure compounds and for their dispersions in solid matrices (zeonex) than those recorded for toluene and dichloromethane solutions of the studied phenoxazine-N-hexylacridone isomers. The obtained experimental spectroscopic and structural data were confronted with theoretical predictions based on DFT calculations.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10402 - Inorganic and nuclear chemistry

Projekt

<a href="/cs/project/GA17-02578S" target="_blank" >GA17-02578S: Elektronově deficitní [n]fenaceny jako nové organické polovodiče: syntéza, funkcionalizace, charakterizace a studium tenkých filmů</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2020

Kód důvěrnosti údajů

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

Název periodika

Physical Chemistry Chemical Physics

ISSN

1463-9076

e-ISSN

—

Svazek periodika

22

Číslo periodika v rámci svazku

16

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

13

Strana od-do

8522-8534

Kód UT WoS článku

000537175100024

EID výsledku v databázi Scopus

2-s2.0-85084167600