Przemyslaw Data

Silesian University of Technology · Department of Physical Chemistry and Technology of Polymers

This work presents an investigation of three xanthone derivatives as the emitters for organic light-emitting diode applications. Through extensive photophysical and electrochemical studies, the thermally activated delayed fluorescence effect was observed and further applied in devices. Due to the substantial ΔEST gap, the final efficiency of the OL...

Hyperfluorescence (HF), a relatively new phenomenon utilizing excitons transfer between two luminophores, requires careful pairwise tuning of molecular energy levels and is proposed to be the crucial step toward the development of new, highly effective OLED systems. To date, barely a few HF yellow emitters with desired narrowband emission but moder...

Previous works reported the synthesis of donor‐acceptor‐donor molecules based on dibenzophenazine acceptor group, presenting thermally activated delayed fluorescent (TADF) properties and their application in the assembly of highly efficient electroluminescent devices. Herein, we focus on the characterisation of charge carrier species through UV‐Vis...

A dual-photofunctional organogermanium compound based on a donor–acceptor–donor architecture that exhibits thermally activated delayed fluorescence and mechano-responsive luminochromism has been developed. The developed compound was successfully applied as an emitter...

A new thermally activated delayed fluorescence (TADF) compound based on a donor–acceptor (D–A) architecture (D = phenox- azine; A = dibenzo[a,j]phenazine) has been developed, and its photophysical properties were characterized. The D–A compound is applicable as an emitting material for efficient organic light-emitting diodes (OLEDs), and its extern...

Although bowl‐shaped N‐pyrrolic polycyclic aromatic hydrocarbons (PAHs) can achieve excellent electron‐donating ability, their application for optoelectronics is hampered by typically low photoluminescence quantum yields (PLQYs). To address this issue, we report the synthesis and characterization of a series of curved and fully conjugated nitrogen‐...

Although bowl‐shaped N‐pyrrolic polycyclic aromatic hydrocarbons (PAHs) can achieve excellent electron‐donating ability, their application for optoelectronics is hampered by typically low photoluminescence quantum yields (PLQYs). To address this issue, we report the synthesis and characterization of a series of curved and fully conjugated nitrogen‐...

The primary reason behind the search for novel organic materials for application in thermoelectric devices is the toxicity of inorganic substances and the difficulties associated with their processing for the production of thin, flexible layers. When Thomas Seebeck described a new phenomenon in Berlin in 1820, nobody could have predicted the future...

Light-activated antimicrobial coatings are currently considered to be a promising approach for the prevention of nosocomial infections. In this work, we present a straightforward strategy for the deposition of a photoactive biocidal organic layer of zinc (tetraamino)phthalocyanine (ZnPcNH2) in an electrochemical oxidative process. The chemical stru...

A new family of thermally activated delayed fluorescence (TADF) emitters based on a twisted donor–acceptor (D–A) dyad scaffold comprising of dihydrophenazasiline (D) and pyrido[2,3‐ b ]pyrazine (A) has been developed, and their properties have been investigated. Time‐resolved spectroscopic analysis in matrices revealed the detailed photophysical pr...

The introduction of pyrrolic nitrogen dopants into the central sites of polycyclic aromatic hydrocarbons (PAHs) often gives rise to characteristic bowl-shaped structures due to the simultaneous introduction of 5- and/or 7-membered cycles. Although the incorporation of these heteroatoms achieves excellent electron-donating ability, the application o...

Poly(3-hexylthiophene) thin films containing carbon-based nanostructures, i.e. fullerenes such as Buckminsterfullerene (C60) or phenyl-C61-butyric acid methyl ester (PCBM), or single-walled carbon nanotubes, were investigated as heterogeneous photosensitizers producing singlet oxygen...

Exploring the design principle for switching thermally activated delayed fluorescence (TADF) and room temperature phosphorescence (RTP) is a fundamentally imporant research in developing triplet-mediated photofunctional organic materials. Herein systematic studies...

Hyperfluorescence (HF), a relatively new phenomenon utilizeing excitones transfer between two luminophores, requires careful pairwise tuning of molecular energy levels and is proposed to be the crucial step towards the...

Polycyclic aromatic hydrocarbons (PAHs) with centrally positioned nitrogen dopants possess a unique curved structure and strong electron-donating features. However, the lack of tools to synthetically affect their bandgap engineering and charge-transfer (CT) characteristic is detrimental to their future optoelectronics use because of usually low PLQ...

Two donor-acceptor (D-A) s-tetrazine derivatives are reported, their electrochemical, optical and spectroelectrochemical (UV-Vis and EPR) analysis is carried out. Thiophene ring, in the case of TzTH and terthiophene unit for Tz3TH serves as a donor group which are linked with s-tetrazine ring via nonconjugated spacer. Investigations have shown that...

Exploring design principle for switching thermally activated dealyed fluorescecne (TADF) and room temperature phosphorescence (RTP) is a fundamentally imporant research in developing triplet-mediated photofunctional organic materials. Herein systematic studies on the regioisomeric and substituents effects in a twisted donor–acceptor–donor (D–A–D) s...

A new twisted donor-acceptor-donor (D-A-D) multi-photofunctional organic molecule comprising phenoselenazine as the electron donor (Ds) and dibenzo[a,j]phenazine (DBPHZ) as the electron acceptor (A) has been developed. The developed selenium-incorporated D-A-D compound features multi-color polymorphism, distinct mechanochromic luminescence, chemica...

Novel electron‐donor–acceptor‐donor (D–A–D) compounds comprising of dibenzo[a,j ]phenazine as the central acceptor core and two 7‐membered diarylamines (i.e., iminodibenzyl and iminostilbene) as the donors have been designed and synthesized. The investigation of their physicochemical properties revealed the impact of C2‐insertion into well‐known ca...

Two highly efficient commercial organic photosensitizers—azure A (AA) and 5-(4-aminophenyl)-10,15,20-(triphenyl)porphyrin (APTPP)—were covalently attached to the glass surface to form a photoactive monolayer. The proposed straightforward strategy consists of three steps, i.e., the initial chemical grafting of 3-aminopropyltriethoxysilane (APTES) fo...

div> A new twisted donor–acceptor–donor (D–A–D) multi-photofunctional organic molecule comprising of phenoselenazine as the electron-donors (Ds) and dibenzo[a,j]phenazine (DBPHZ) as the electron-acceptor (A) has been developed. The developed selenium-incorporated D–A–D compound is featured with multi-color polymorphism, distinct mechanochromic lum...

Acridones have found their role in luminescent materials for OLEDs. Most interestingly, showing potential as weak charge transfer thermally activated delayed fluorescence (TADF) emitters, providing narrow photoluminescence. In this work, we present a comprehensive study of donor-acceptor-donor (D-A-D) acridone-amine derivatives showing TADF and UV...

Room temperature phosphorescence materials offer great opportunities for applications in optoelectronics, due to their unique photophysical characteristics. However, heavy-atom-free organic emitters that can realize distinct electrophosphorescence are rarely exploited. Herein a new approach for designing heavy-atom-free organic room temperature pho...

A new family of emissive donor–acceptor–donor (D–A–D) compounds has been developed by introducing two electron-donors into the 7,8-diaza[5]helicene core as a novel helical electron acceptor. The X-ray crystallographic analyses revealed the uniquely twisted and helical structures of these compounds in the solid states. Notably, some D-A-D compounds...

A new thermally activated delayed fluorescence (TADF)‐displaying macrocyclic compound m‐1 comprising of two electron‐donors (N,N’‐diphenyl‐m‐phenylenediamine) and two electron‐acceptors (dibenzo[a,j]phenazine) has been synthesized. The macrocycle developed herein is regarded as a regioisomer of the previously reported TADF macrocycle p‐1, which has...

In this work, we present how a small change in molecular structure can affect the electrochemical stability of organic compounds. A new electron donor‐acceptor‐donor‐acceptor (D‐A‐D‐A) macrocyclic π‐conjugated compound (tBuMC) comprising of dibenzophenazine as As and N,N’‐bis(t‐butylphenyl)‐p‐phenylenediamines as Ds has been synthesized. The photop...

Room temperature phosphorescence materials offer great opportunities for applications in optoelectronics, due to their unique photophysical characteristics. However, purely organic emitters that can realize distinct electrophosphorescence are rarely exploited. Herein a new approach for designing heavy-atom-free organic room temperature phosphoresce...

Electron-deficient azaaromatics play crucial roles in organic material fields. Therefore, the development of synthetic methods for electron-deficient azaaromatics and the exploration of their properties and functions is important for the advancement of materials sciences and related research fields. In this Feature Article, we describe new syntheti...

A selenophene-containing fullerene dyad (C60Se) was electrochemically co-deposited with bis-selenophene (BisSe) to form a visible light absorbing poly(selenophene) layer with incorporated fullerene photosensitizers on platinum (Pt) or indium-tin oxide (ITO) substrates. The resulting photoactive films (P(C60Se_BisSe)) were characterized by cyclic vo...

A facile efficient synthetic tool, Buchwald-Hartwig cross-coupling reaction, in the synthesis of 1,2,4,5-tetrazines is presented. The important factors of Buchwald-Hartwig cross-coupling reaction for tetrazine functionalization are discussed, which could be of practical importance for researchers performing Buchwald-Hartwig coupling reaction on dif...

A new class of thermally activated delayed fluorescent donor–acceptor–donor–acceptor (D–A–D–A) π-conjugated macrocycle comprised of two U-shaped electron-acceptors (dibenzo[a,j]phenazine) and two electron-donors (N,N’-diphenyl-p-phenyelendiamine) has been rationally designed and successfully synthesized. The macrocyclic compound displayed polymorph...

A series of cobalt (II) porphyrin complexes modified with carbazole rings at one or more meso positions of the macrocycle were synthesized and characterized as to their spectroscopic and basic electrochemical properties in non-aqueous media. The effect of the number and position (syn and anti) of carbazole groups on the complexes properties were in...

We report a strategy for positively influencing the conformation of thermally activated delayed fluorescence (TADF) molecules containing phenothiazine and dibenzothiophene-S,S-dioxide units.

The time-resolved photophysial anyalysis of a multi-color-chaning mechanochromic luminescent compound has been disclosed, which reveals distinct different emission paths to boost TADF and RTP of the emitter depending on its molecule conformations. Furthermore, by making the use of the obtained knowledge here, we also present the possibility to cont...

Herein we report the investigation of non-doped exciplex formed in blends of 2,4,6-Tris[3-(diphenylphosphinyl)phenyl]-1,3,5-triazine (PO-T2T), working as the one-electron acceptor molecule, with different electron donors. The emission of these exciplexes spans from blue to orange-red, and shows clear contribution from thermally activated delayed fl...

A novel and unexpected convenient one‐pot synthesis of 1,2,3,4‐thiatriazoles has been discovered while investigating the classical tetrazine “Pinner synthesis”. The synthetic route starts from commercially‐available nitrile derivatives and gives good to high yields (51–80 %) with no need to isolate any thioacylating agents. The crucial impact of th...

Organic emitting compounds that are based onp-conjugated skeletons have emerged as promising next-gen-eration materials for application in optoelectronic devices. Inthis Minireview, recent advances in the development of or-ganic emitters that irradiate room-temperature phosphores-cence and/or thermally activated delayed fluorescence withextraordina...

Here, we present a sensible method of the acquisition and analysis of time-resolved photoluminescence using an ultrafast iCCD camera. This system enables the acquisition of photoluminescence spectra covering the time regime from nanoseconds up to 0.1 s. This enables us to follow the changes in the intensity (decay) and emission of the spectra over...

A method for producing simple and efficient thermally-activated delayed fluorescence organic light-emitting diodes (OLEDs) based on guest-host or exciplex donor-acceptor emitters is presented. With a step-by-step procedure, readers will be able to repeat and produce OLED devices based on simple organic emitters. A patterning procedure allowing the...

Exploration of optoelectronic properties of novel phosphorus-embedded π-conjugated compounds would provide us with fundamental information about the design of hitherto unknown electroactive organic materials. Herein, detailed photophysical and electrochemical profiles of a series of benzene-cored diketophosphanyl compounds were investigated with st...

To provide high exciton utilization in organic light emitting diodes, phthalimide derivatives were designed and synthesized as exciplex-forming materials. Due to high triplet levels (2.92–3.11 eV) and ionization potentials (7.18–7.29 eV), the developed phthalimide derivatives were found to be not only appropriate accepting materials for the formati...

Cyclic voltammetry (CV) is a technique used in the analysis of organic compounds. When this technique is combined with electron paramagnetic resonance (EPR) or ultraviolet-visible and near-infrared (UV-Vis-NIR) spectroscopies, we obtain useful information such as electron affinity, ionization potential, band-gap energies, the type of charge carrier...

In the presented work, two spectroelectrochemical techniques are discussed as tools for the analysis of the structural changes occurring in the molecule on the vibrational level of energy. Raman and IR spectroelectrochemistry can be used for advanced characterization of the structural changes in the organic electroactive compounds. Here, the step-b...

Electrochemical impedance spectroscopy (EIS) was used for advanced characterization of organic electroactive compounds along with cyclic voltammetry (CV). In the case of fast reversible electrochemical processes, current is predominantly affected by the rate of diffusion, which is the slowest and limiting stage. EIS is a powerful technique that all...

Thianthrenes have been nearly forgotten as phosphors in recent years, but are now coming back, showing their strong potential in luminescent applications. Here, we present a comprehensive photophysical study of a carbazolyl derivative of thianthrene in different matrices and environments. The diffusion of oxygen is slowed down in the rigid environm...

Thermally-activated delayed fluorescence has been found in a group of tricarbazolylamines which are purely electron-donating, non-charge transfer (CT) molecules. We show that the reverse intersystem crossing step in these materials is mediated through upper triplet states. Reverse internal conversion is shown to be the thermally-activated mechanism...

Here, we discuss the influence of the crystal structure on the photophysical properties of two new TADF emitters containing a non-planar helical moiety. The presence of solvent in the crystal...

A series of bisbenzofuro[2,3-b:3’,2’-e]pyridines (BBZFPys) bearing a chlorine functionality have been efficiently synthesized through a Pd-catalyzed double oxidative intramolecular C–H/C–H coupling of mono-chlorinated 2,6-diaryloxypyridines. The subsequent Buchwald-Hartwig amination of the chlorinated BBZFPys allowed for the access to a new class o...

The photophysics of an exciplex state, formed between a small molecule and a polymer, is investigated in this work. The results obtained with this blend show the strong potential of polymer-small molecule blends for triplet harvesting in organic light emitting diodes (OLEDs) via thermally-activated delayed fluorescence. The exciplex formed between...

It is demonstrated that naphthalene diimide core disubstituted with triphenylamine can be used as a Thermally Activated Delayed Fluorescence emitter in Organic Light Emitting Diodes. Detailed spectroscopic studies demonstrated unusual host effects on the photophysical properties of this material. In particular, we were able to deduce recombination...

A novel twisted donor–acceptor–donor (D–A–D) π-conjugated compound that contains flexible and moderately-electron-donating units has been designed and synthesized. It exhibited not only multi-color-changing mechanochromic luminescence and thermally activated delayed fluorescence, but also, unexpectedly, room-temperature phosphorescence in a host la...

This work shows a study of two organic molecules with very similar, large singlet-triplet gap of which one is a TADF emitter and the other an RTP emitter. By investigation of photophysical properties of these compounds, it is possible to explain their distinct behavior. Properties are studied in non-polar polymer and OLED host with further device f...

In this work, we present the electrochemical polymerisation process of triarylamine-xanthone derivatives and behaviour of the formed polymers using various potentiodynamic techniques. The formed electropolymers have limited conjugation but show very promising electrochromic behaviour. Furthermore, by coupling the electrochemical analysis with each...

We report on the engineering of full thermally activated delayed fluorescence – based white organic light emitting diodes (W-OLEDs) composed of three emitters (2,7-bis(9,9-dimethyl-acridin-10-yl)-9,9-dimethylthioxanthene-S,S-dioxide (DDMA-TXO2), 2,7-bis(phenoxazin-10-yl)-9,9-dimethylthioxanthene-S,S-dioxide (DPO-TXO2) and 3,11-di(10H-phenoxazin-10-...

A number of commercial organic compounds (m-MTDATA, PBD, CBP, TAPC, NPB, TPBi, etc) as well as several donor-acceptor-donor (D-A-D) compounds were investigated by cyclic voltammetry and electrochemical impedance spectroscopy. The compounds were chosen as they are promising components of small-molecule-based high efficiency Thermally Activated Delay...

In this work we present electropolymerization of monomers of an unusual type using N-linked carbazole units to limit their conjugation. The polymers thus obtained have limited conjugation through the backbone. Using donor-acceptor-donor (D-A-D) and donor-donor-donor (D-D-D) monomers we evaluate the effects of the presence (or absence) of charge tra...

Previous research in our group showed that tellurophenes with pinacolboronate (BPin) units at the 2- and/or 5-positions displayed efficient phosphorescence in the solid state, both in the presence of oxygen and water. In this current study, we show that lumi-nescence from a tellurophene is possible when various aryl-based substituents are present,...

The Front Cover picture shows a chimera illuminated by the fluorescence emission of thioxanthone, the aromatic carbonyl studied here. Due to singlet and triplet excitations in close energetic vicinity, its photophysics exhibits a chimeric behavior. More information can be found in the Communication by P. Gilch and co-workers (DOI: 10.1002/cphc.2017...

The front cover artwork is provided by the groups of Prof. Peter Gilch (HHU Düsseldorf) and Prof. Andrew Monkman (Durham University). The image shows a chimera illuminated by the fluorescence emission of thioxanthone, the aromatic carbonyl studied here. Due to singlet and triplet excitations in close energetic vicinity, its photophysics exhibits a...

The efficiency of organic light emitting diodes crucially depends on triplet harvesters. These accept energy from triplet correlated electron hole pairs and convert it into light. Here experimental evidence is given that simple aromatic carbonyls, such as thioxanthone, could serve this purpose. In these compounds the emissive 1ππ* excitation may r...

Intense, simultaneous, room temperature phosphorescence (RTP) and thermally activated delayed fluorescence (TADF) is observed in a series of donor-acceptor-donor (D-A-D) molecules. This dual-luminescence is stronger in the "angular" isomers, compared to their "linear" regioisomers, which is consistent with an enhanced intersystem crossing (ISC) in...

2,7- and 3,6- substituted carbazole and triphenylamine chalcogenophene (Se, Te) derivatives and their electrodeposited polymers are investigated using electrochemical and UV-Vis-NIR / ESR spectroelectrochemical methods. Major differences in the case of oxidation and electropolymerization behavior between monomers and related polymers are shown. Se...