Publications

M. Urban, P. H. Marek-Urban, K. Durka, S. Luliński, P. Pander, A. P. Monkman

Angewandte Chemie International Edition, 2023, 86, 12714-12722

DOI: 10.1002/anie.202217530

SO2B – a high triplet (T1 = 3.05 eV) strongly electron-accepting boracycle was successfully utilised in thermally activated delayed fluorescence (TADF) emitters PXZ-Dipp-SO2B and CZ-Dipp-SO2B. We demonstrate the near-complete separation of highest occupied and lowest unoccupied molecular orbitals leading to a low oscillator strength of the S1→S0 CT transition, resulting in very long ca. 83 ns and 400 ns prompt fluorescence lifetimes for CZ-Dipp-SO2B and PXZ-Dipp-SO2B, respectively, but retaining near unity photoluminescence quantum yield. OLEDs using CZ-Dipp-SO2B as the luminescent dopant display high external quantum efficiency (EQE) of 23.3% and maximum luminance of 18600 cd m-2 with low efficiency roll off at high brightness. For CZ-Dipp-SO2B, reverse intersystem crossing (rISC) is mediated through the vibronic coupling of two charge transfer (CT) states, without involving the triplet local excited state (3LE), resulting in remarkable rISC rate invariance to environmental polarity and polarisability whilst giving high organic light-emitting diode (OLED) efficiency. This new form of rISC allows stable OLED performance to be achieved in different host environments.

K. Durka, P. H. Marek-Urban, J. Krajewska, A. E. Laudy, K. Woźniak, S. Luliński

RSC Advances, 2022, 12, 23099-23117

DOI: 10.1039/D2RA03910A

Two isomeric benzosiloxaborole derivatives 4,4-dimethyl-2-oxazolin-2-yl substituents attached to the aromatic rings were obtained. Both compounds were prone to hydrolytic cleavage of oxazoline ring after initial protonation or methylation of the nitrogen atom. Compound bearing N-ammoniumalkyl ester underwent conversion to a unique macrocyclic dimer due to siloxaborole ring opening. Furthermore, an unexpected 4-electron reduction of oxazoline ring occurred giving rise to an unprecedented 7-membered heterocyclic system.

K. Durka, P. H. Marek-Urban, K. Nowicki, J. Drapała, K. N. Jarzembska, P. Łaski, A. Grzelak, M. Dąbrowski, K. Woźniak, S. Luliński

Chemistry - A European Journal, 2022, e202104492

DOI: 10.1002/chem.202104492

The approach to a series of six- and seven-membered oxaboraheterocycles based on naphthalene or biphenyl backbones was developed. Selected compounds were used as a basis for luminescent complexes with 8-hydroxyquinoline. A strong phase-dependent variation of emission band maximum and photoluminescence quantum yield (10-95%) was observed, which was rationalized in terms of specific aggregation effects.

K. Durka, K. Kazimierczuk, S. Luliński

Microporous and Mesoporous Materials, 2022, 337, 111914

DOI: 10.1016/j.micromeso.2022.111914

The utility of the nonlinear diboronic acid for the preparation of Covalent Organic Frameworks was investigated. Despite significant deviation of boronic groups from the colinear arrangement, a highly crystalline porous material DBSO-COF was obtained by dehydrative polycondensation HHTP. PXRD studies supported by periodic DFT modelling revealed the formation of the 2D honeycomb-type lattice with eclipsed stacking model. The antiparallel orientation of neighboured layers is strongly favoured owing to dipole-dipole and CH…O interactions of sulfone moieties. This gives the net stabilization energy of 45 kJ∙mol-1 per single sulfone motif, being primarily responsible for the effective formation of the ordered network.

P. H. Marek-Urban, M. Urban, M. Wiklińska, K. Paplińska, K. Woźniak, A. Blacha-Grzechnik, K. Durka

The Journal of Organic Chemistry, 2021, 86, 12714-12722

DOI: 10.1021/acs.joc.1c01254

Short description: We present new strategy for the development of efficient heavy-atom free singlet oxygen photosensitizers based on rigid borafluorene scaffolds. Physicochemical properties of borafluorene complexes can be easily tuned through the choice of ligand, thus allowing to explore numerous organoboron structures as potent 1O2 sensitizers.

P. Pacholak, J. Krajewska, P. Wińska, J. Dunikowska, U. Gogowska, J. Mierzejewska, K. Durka, K. Woźniak, A. E. Laudy, S. Luliński

RSC Advances, 2021, 11, 25104-25121

DOI: 10.1039/d1ra04127d

Short description: The synthesis of potassium 6-hydroxy-7-chloro-1,1-dimethyl-3,3-difluorobenzo-1,2,3-siloxaborolate from readily available 4-bromo-2-chlorophenol was developed. This compound proved useful in various derivatizations resulting in a wide range of O-functionalized benzosiloxaboroles. Investigation of biological activity of obtained compounds revealed that some benzoate and most benzenesulfonate derivatives exhibit high activity against Gram-positive cocci such as methicillin-sensitive Staphylococcus aureus ATCC 6538P as well as methicillin-resistant S. aureus ATCC 43300 with the MIC values in the range of 0.39-3.12 mg/L. Some benzenesulfonate derivatives showed also potent activity against Enterococcus faecalis ATCC 29212 and E. faecium ATCC 6057 with MIC = 6.25 mg/L. Importantly, for the most promising cocci-active benzenesulfonate derivatives the obtained MIC values were far below the cytotoxicity limit determined with respect to human normal lung fibroblasts (MRC-5).

K. Nowicki, P. Pacholak, S. Luliński

Molecules 2021, 26, 5464

DOI: 10.3390/molecules26185464

The review covers the chemistry of organoboron heterocycles structurally related to benzoxaboroles where one of the carbon atoms in a boracycle or a fused benzene ring is replaced by a heteroelement such as boron, silicon, tin, nitrogen, phosphorus, or iodine. The information on synthetic methodology as well as the basic structural and physicochemical characteristics of these emerging heterocycles is complemented by a presentation of their potential applications in organic synthesis and medicinal chemistry.

P. Pacholak, K. Gontarczyk, R. Kamiński, K. Durka, S. Luliński

Chemistry European Journala, 2020, 26, 12758–12768

DOI:10.1002/chem.202001960

Short description: Two covalent organic frameworks comprising Lewis basic PIII centers and Lewis acidic boron atoms were prepared. Obtained materials exhibit significant sorption of dihydrogen, methane and carbon dioxide. They were exploited as solid- state ligands for coordination of Pd0 centers. The DFT calculations on framework–guest interactions revealed that the behavior of adjacent boron and phosphorus/phosphine oxide centers is reminiscent of that found in Frustrated Lewis Pairs and may improve sorp- tion of selected molecules.

M. Urban, K. Durka, P. Górka, G. Wiosna-Sałyga, K. Nawara, P. Jankowski, S. Luliński,

Honoured as ‘hot article’

Dalton Transactions, 2019, 48, 8642-8663.

DOI: 10.1039/C9DT01332F

Short description: A series of 8 luminescent borafluorene complexes were extensively studied both experimentally and theoretically in order to elucidate the effect of organoboron moiety rigidification on physicochemical properties of these compounds. Due to spiro geometry of boron atom, borafluorene and ligand units are perpendicularly aligned, what considerably affects the flexibility of the molecule as well as its solid-state structure. Through the comparative analysis with close diphenyl analogues, we show how these structural features influences thermal, photoluminescent and charge mobility behaviour of studied compounds.

K. Durka, M. Urban, M. Dąbrowski, P. Jankowski, T. Kliś, S. Luliński

ACS Omega, 2019, 4, 2482−2492

DOI: 10.1021/acsomega.8b03290

Short description: A series of isomeric isomeric boronated acridinium salts and their zwitterionic trifluoroborato counterparts have been prepared and comprehensively characterized. They proved to be effective organic photocatalysts in selected addition reactions.

K. Durka, A. E. Laudy, Ł Charzewski, M. Urban, K. Stępień, S. Tyski, K. A. Krzyśko, S. Luliński

European Journal of Medicinal Chemistry, 2019, 171, 11-24

DOI: 10.1016/j.ejmech.2019.03.028

Short description: A series of benzosiloxaboroles with varying substitution patterns were obtained and their biological properties were comprehensively studied in order to elucidate the structural factors that affect their bioactivities. The obtained compounds demonstrate KPC/AmpC β-lactamases enzyme inhibitory activity.

P. Tomaszewski, M. Wiszniewski, K. Gontarczyk, P. Wieciński, K. Durka,
S. Luliński

Polymers, 2019, 11, 1070-1082

DOI: doi.org/10.3390/polym11061070

Short description: Lithium tetrakis(4-boronatoaryl)borates were subjected to polycondensation reactions with selected polyhydroxyl leading to porous polymers exhibiting relatively good sorption of H2.

K. Durka, B. Górski, K. Błocki, M. Urban, K. Woźniak, M. Barbasiewicz, S. Luliński

The Journal of Physical Chemistry A, 2019, 123, 8674−8689

DOI:10.1021/acs.jpca.9b07360

Short description: A series of five bis(salicylaldehydes), including four isomeric compounds based on a benzene scaffold were investigated in order to elucidate the impact of resonance effects and intramolecular hydrogen bonds (HBs) on the macroscopic properties of these systems. Obtained results indicate that the optical properties of bis(salicylaldehydes) are directly transferable to more advanced materials such bis(salicylaldimines) and luminescent complexes.

K. Durka, M. Urban, M. Czub, M. Dąbrowski, P. Tomaszewski, S. Luliński

Back cover

Dalton Transactions, 2018, 47, 3705−3716

DOI: 10.1039/C7DT04858K

Short description: Intramolecular activation of the Si–H bond in arylsilanes by selected ortho-assisting functional groups based on boron, carbon and phosphorus was investigated experimentally and by means of theoretical calculations.

M. Urban, P. Górka, K. Nawara, K. Woźniak, K. Durka,* S. Luliński,

Front inside cover

Dalton Transactions, 2018, 47, 15670-15684

DOI: 10.1039/C8DT03197E

Short description: The effect of molecular conformation on the luminescence properties of two sterically congested diboron complexes with 8-oxyquinolato ligands are studied. We have shown that the luminescence quantum efficiency can be tuned by the control of molecular conformation in solution and solid state.

P. Tomaszewski, M. Wiszniewski, J. Serwatowski, K. Woźniak, K. Durka, S. Luliński

Dalton Transactions, 2018, 47, 16627-16637

DOI: http://dx.doi.org/10.1039/C8DT04068K

Short description: A novel general protocol for the preparation of functionalized (COOH, CHO, C(O)NHtBu, B(OH)2) tetraphenyl- and tetrakis(4’-biphenylyl)borates is reported. X-ray crystal structures of selected salts show a strong effect of both the cation and the kind of functional group on supramolecular architecture ranging from direct incorporation of lithium cations into the formation of supramolecular network, less direct effect of structure distortions through cation…C(π) interactions, to porous structure with disordered lithium cations residing in crystal cavities.

3. M. Czub, K. Durka, S. Luliński, J. Łosiewicz, J. Serwatowski, M. Urban, K. Woźniak

European Journal of Organic Chemistry, 2017, 818–826

DOI: 10.1002/ejoc.201601328

Short description: We have synthesised a series of fluorinated benzosiloxaboroles bearing synthetically useful formyl and cyano groups. These compounds have been obtained by multistep syntheses starting with simple halogenated benzenes.

M. Urban, K. Durka, P. Jankowski, J. Serwatowski, S. Luliński

Journal of Organic Chemistry, 2017, 82, 8234−8241

DOI: 10.1021/acs.joc.7b01001

Short description: We have synthesised a series of very efficient fluorescence emitters (QY up to 83%) - bisboranil derived from 1,5-dihydroxynaphthalene-2,6-dicarboxaldehyde. Their photophysical properties can be easily tuned in a wide range by the variation of substituents.

K. Gontarczyk, W. Bury, J. Serwatowski, P. Wieciński, K. Woźniak, K. Durka, S. Luliński

ACS Appl. Mater. Interfaces, 2017, 9, 31129−31141

DOI: 10.1021/acsami.7b09061

Short description: We have successfully synthesised hybrid boron-triazine porous COF material. The PXRD studies supported by periodic DFT modeling in Crystal09 package revealed the formation of crystalline 2D honeycomb-type lattices with eclipsed stacking models. The interactions between layers are enhanced by the stacking of triazine and boroxine rings.

K. Durka, K. Gontarczyk, S. Luliński, J. Serwatowski, K. Woźniak

Crystal Growth&Design., 2016, 16, 4292−4308

DOI: 10.1002/ejoc.201601328

Short description: We present detailed investigations of the structure−energy−property relationships for a series of oligothienylsilanes using a combination of experimental and computational procedures. Despite the fact that all studied systems show a very high level of structural similarity, they revealed distinct physicochemical behavior. This is due to a different distribution of C−H···C(π), S···C(π), and S···S interactions within the corresponding crystal structures.

A. Brzozowska, P. Ćwik, K. Durka, T. Kliś, A. E. Laudy, S. Lulińkski, J. Serwatowski, S. Tyski, M. Urban, W. Wróblewski

Organometallics, 2015, 34, 2924–2932

DOI: 10.1039/C4TC02350A

Short description: In this manuscript we present the synthesis and physicochemical properties of benzosiloxaboroles, the silicon analogues of an important class of heterocyclic compounds - benzoxaboroles. The presence of a B–O–Si linkage results in increased Lewis acidity with respect to the analogous benzoxaboroles. Selected compounds show good antifungal activity, and thus they are potential small-molecule therapeutic agents. They can also serve as effective receptors for biologically relevant diols under neutral pH conditions.

I. Steciuk, K. Durka, K. Gontarczyk, M. Dąbrowski, S. Luliński, K. Woźniak

Dalton Transactions, 2015, 44, 16534-16546

DOI: 10.1039/C4TC02350A

Short description: We present new group of boron heterocycles: Pyridoxaboroles – fused heterocyclic systems composed of pyridine and five-membered oxaborole rings. Single-crystal X-ray analysis revealed the formation of either H-bonded chains or unique 1D coordination polymer based on N–B dative bonds between monomeric molecules.

K. Durka, I. Głowacki, S. Luliński, B. Łuszczyńska, J. Smętek, P. Szczepanik, J. Serwatowski, U. E. Wawrzyniak, G. Wesela-Bauman, E. Witkowska, G. Wiosna-Sałyga, K. Woźniak

Journal of Material Chemistry C, 2015, 3, 1354–1364.

DOI: 10.1039/C4TC02350A

Short description: In this work we have studied the optical properties of obtained by us very efficient oxyquinolinato green-light emitters (QY = 63%) based on 9,10-diboraanthracene. We suggest that the luminescent properties of the studied compounds are affected by their specific structural properties – two different conformers were found. The obtained compounds were tested as emitters for the construction of organic light emitting diodes (OLEDs).

G. Wesela-Bauman, M. Urban, S. Luliński, J. Serwatowski, K. Woźniak

Organic and Biomolecular Chemistry, 2015, 13, 3268-3279

DOI: 10.1039/C4OB02545H

Short description: We present the synthesis of a series of di- tri- and tetraboronic acids based on respective phenyl- and thienylsilane cores. The optimal protocols involved lithiation of respective arylsilane precursors using either deprotonative lithiation or halogen/lithium exchange with n-BuLi followed by treatment of resultant intermediates with B(OiPr)₃.

K. Gontarczyk, K. Durka, P. Klimkowski, S. Luliński, J. Serwatowski, K. Woźniak

Journal of Organometallic Chemistry, 2015, 783, 1-9

DOI: 10.1016/j.jorganchem.2015.01.024

Short description: We present the synthesis of a series of di- tri- and tetraboronic acids based on respective phenyl- and thienylsilane cores. The optimal protocols involved lithiation of respective arylsilane precursors using either deprotonative lithiation or halogen/lithium exchange with n-BuLi followed by treatment of resultant intermediates with B(OiPr)₃.

K. Durka, S. Luliński, M. Dąbrowski, J. Serwatowski

European Journal of Organic Chemistry, 2014, 4562–4570

DOI: 10.1002/ejoc.201402320

Short description: The unexpected effect of carbon dioxide on halogen-lithium exchange (HLE) reactions of selected haloarenes with t-BuLi was investigated. In the aliphatic hydrocarbon solvent (pentane) the HLE does not occur at ca. –70 °C but, surprisingly, pouring the mixture of reactants onto dry ice and subsequent aqueous acidic hydrolysis gave carboxylic acids resulting from the quench of the first-formed aryllithiums with carbon dioxide.

K. Durka, K. N. Jarzembska, S. Luliński, J. Smętek, J. Serwatowski, K. Woźniak

Acta Crystallographica Section B, 2014, 70, 157–171

DOI: 10.1107/S2052520613034987

Short description: A competition between hydrogen (O–H…O, O–H…F) and halogen (Cl…Cl, O…Br) bonding interactions influences the molecular arrangement in the crystal structures of a series of boranthrenes. A substitution with an appropriate halogen atom enables fine-tuning of the strength of the interactions and occurrence of either halogen or hydrogen bonds.

K. Durka, S. Luliński, J. Serwatowski, K. Woźniak

Organometallics, 2014, 33, 1608–1616

DOI: 10.1021/om401146p

Short description: The solid-state and solution structural properties and acidity of a series of fluorinated 1,2-phenylenediboronic acids were investigated. In solid state they tend to form semi-anhydrides with strong Lewis acidic Boron centres. Furthermore, molecules can dimerize by aggregation of boronic groups, which leads to the formation of an uncommon 8-membered B4O4 ring. The enhanced acidity of 1,2-phenylenediboronic acids can be rationalized in terms of a synergic effect of two adjacent boronic groups.

G. Wesela-Bauman, S. Parsons, J. Serwatowski, K. Woźniak

CrystEngComm, 2014, 16, 10780-10790

DOI: 10.1039/C4CE01730G

Short description: The crystal and molecular structure of diarylborinic 8-oxyquinolinate has been determined at room temperature at pressures ranging from ambient to 4.9 GPa in approximately 1 GPa steps. The crystal cell volume decreased isotropically to 80% during compression. Further analysis based on the Marcus model showed that electron and hole transport properties are not affected in the same way by the compression.

G. Wesela-Bauman, S. Luliński, J. Serwatowski, K. Woźniak

Physical Chemistry Chemical Physics, 2014, 16, 22762-22774

DOI: 10.1039/C4CP02606C

Short Description: Single crystal X-ray structures of two polymorphs of diarylborinic 8-oxyquinolinate have been established and analysed for the first time. The main differences between both forms are intermolecular interactions and their impact on the charge transporting properties of both polymorphs which was evaluated through Marcus theory.

K. Durka, K. N. Jarzembska, R. Kamiński, S. Luliński, J. Serwatowski, K. Woźniak

Crystal Growth&Design, 2013, 13, 4181–4185

DOI: 10.1021/cg401087j

Short description: A nanotubular crystal network of a small-molecule compound, 1,2-phenylenediboronic acid, constituting a hydrogen-bonded organic framework (HOF) architecture, is presented. In contrast to the carbon nanotubes, the intermolecular connections are based strictly on hydrogen-bonding interactions. Such channels host water clusters similar to the ones found in the hexagonal structures of ice. Structural uniqueness is additionally enhanced by the existence of the other two crystal phases, characterized by more compact structures.

K. Durka, S. Luliński, J. Smętek, M. Dąbrowski, J. Serwatowski, K. Woźniak

European Journal of Organic Chemistry, 2013, 3023–3032

DOI: 10.1002/ejoc.201300145

Short description: The selectivity of the Br/Li exchange in boron-based functional group-bearing aryl and thienyl boronates was investigated using nBuLi as the lithiating reagent. Calculations performed for lithiation of ortho- and meta-brominated phenyl boronates revealed that ortho-lithiated aryl boronates are thermodynamically more stable but the Br/Li exchange is generally dictated by kinetics which accounts for the variation of selectivity depending on the type of boronate group.

S. Luliński, J. Smętek, K. Durka, J. Serwatowski

European Journal of Organic Chemistry, 2013, 8315–8322

DOI: 10.1002/ejoc.201300868

Short description: The simple general protocol for the synthesis of functionalized 5,10-dihydroxy-5,10-dihydroboranthrene by the treatment of appropriate substituted 2-halophenyl boronates with tBuLi is reported. The reaction occurs apparently via the formation of ortho-lithiated phenyl boronates. The results of DFT calculations indicate that the Br/Li exchange is kinetically more favored than the nucleophilic alkylation of the trivalent boron atom.

G. Wesela-Bauman, P. Ciećwierz, K. Durka, S. Luliński, J. Serwatowski, K. Woźniak

Inorganic Chemistry, 2013, 52, 10846–10859

DOI: 10.1021/ic400729t

Short description: A one-pot protocol has been developed to obtain a series of luminescent heteroleptic diarylborinic complexes bearing the 2-fluoro-3-pyridyl and another aryl group attached to the boron atom chelated with 8-oxyquinolinato ligands. They were used for the as building blocks in the construction of various supramolecular luminescent systems, specifically, those based on the formation of metal-nitrogen dative bond.

E. Borowska, K. Durka, S. Luliński, J. Serwatowski, K. Woźniak

European Journal of Organic Chemistry, 2012, 2208–2218

DOI: 10.1002/ejoc.201101764 8

Short description: Investigation of the thiophene boronates has revealed usefulness of metalation reaction in the synthesis of various lithiated thiophene boronates which are further converted to functionalized thiopheneboronic derivatives. The calculations of transition states have shown that the specific directing effect of boronate groups in 3-thienyl derivatives is due to the intramolecular oxygen–lithium coordination.

K. Durka, K. N. Jarzembska, R. Kamiński, S. Luliński, J. Serwatowski, K. Woźniak

Crystal Growth&Design, 2012, 12, 3720–3724

DOI: 10.1021/cg3005272

Short description: The effect of fluorine substitution on crystal organization in the presence of strong and directional hydrogen bonds was studied in the series of fluorinated p-phenylenediboronic acids. As indicated by the theoretical calculations the structures with greater amount of water are better stabilized. Fluorine substituents tend to interact with the electropositive boron atom. Furthermore, intramolecular interactions significantly affect the torsion angle of the B(OH)2 group.

K. Durka, A. A. Hoser, R. Kamiński, S. Luliński, J. Serwatowski, W. Koźmiński, K. Woźniak

Crystal Growth&Design, 2011, 11, 1835–1845

DOI: 10.1021/cg200032e

Short description: Two polymorphic structures of the model arylboronic azaester we studies using variety of experimental and theoretical tools. Changes of the thermal-expansion tensor and multi-temperature unit-cell X-ray measurements show significant differences between the forms. Theoretical calculations of lattice energies confirms that form I is slightly more stable than form II. The stability of the polymorphs is also reflected in the kinetics of the crystallization process and melting point temperatures.

K. Durka, R. Kamiński, S. Luliński, J. Serwatowski, K. Woźniak

Physical Chemistry Chemical Physics, 2010, 12, 13126–13136

DOI: 10.1039/C0CP00030B

Short description: The unexpected effect of carbon dioxide on halogen-lithium exchange (HLE) reactions of selected haloarenes with t-BuLi was investigated. In the aliphatic hydrocarbon solvent (pentane) the HLE does not occur at ca. –70 °C but, surprisingly, pouring the mixture of reactants onto dry ice and subsequent aqueous acidic hydrolysis gave carboxylic acids resulting from the quench of the first-formed aryllithiums with carbon dioxide.

K. Durka, J. Górka, P. Kurach, S. Luliński, J. Serwatowski

Journal of Organometallic Chemistry, 2010, 695, 2635–2643

DOI: 10.1016/j.jorganchem.2010.08.016

Short description: Silylated functionalized arylboronic acids were converted into corresponding iodinated arylboronic acids in good yields via the electrophilic ipso-desilylation effected with iodine chloride. Polymerization of a representative iodinated arylboronic acid was performed to give highly thermally stable dendrimeric fluorinated poly(phenylene).