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

Irena Kulszewicz-Bajer , Małgorzata Zagórska , Marzena Banasiewicz , Piotr Guńka , Petr Toman , Bolesław Kozankiewicz , Gabriela Wiosna-Sałyga , Adam Proń


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 (givenvs.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 inP1̄ andP21/nspace groups, respectively, with one molecule per asymmetric unit, while m-A crystallized in theP21/cspace 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.

Author Irena Kulszewicz-Bajer (FC / CPCT)
Irena Kulszewicz-Bajer,,
- Chair Of Polymer Chemistry And Technology
, Małgorzata Zagórska (FC / CPCT)
Małgorzata Zagórska,,
- Chair Of Polymer Chemistry And Technology
, Marzena Banasiewicz - [Institute of Physics (IF) [Polish Academy of Sciences (PAN)]]
Marzena Banasiewicz,,
- Instytut Fizyki
, Piotr Guńka (FC / CofIC)
Piotr Guńka,,
- Chair Of Inorganic Chemistry
, Petr Toman - [Institute of Macromolecular Chemistry of the Academy of Sciences of the Czech Republic]
Petr Toman,,
, Bolesław Kozankiewicz - [Institute of Physics (IF) [Polish Academy of Sciences (PAN)]]
Bolesław Kozankiewicz,,
- Instytut Fizyki
, Gabriela Wiosna-Sałyga - [Politechnika Łódzka (PŁ)]
Gabriela Wiosna-Sałyga,,
- Politechnika Łódzka
, Adam Proń (FC / CPCT)
Adam Proń,,
- Chair Of Polymer Chemistry And Technology
Journal seriesPhysical Chemistry Chemical Physics, ISSN 1463-9076, e-ISSN 1463-9084
Issue year2020
Publication size in sheets0.6
ASJC Classification1606 Physical and Theoretical Chemistry; 3100 General Physics and Astronomy
URL https://pubs.rsc.org/en/content/articlelanding/2020/cp/d0cp00521e#!divAbstract
Languageen angielski
10.1039D0CP00521E.pdf 4.1 MB
Score (nominal)100
Score sourcejournalList
ScoreMinisterial score = 100.0, 24-08-2020, ArticleFromJournal
Publication indicators Scopus Citations = 0; Scopus SNIP (Source Normalised Impact per Paper): 2016 = 1.117; WoS Impact Factor: 2018 = 3.567 (2) - 2018=3.963 (5)
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