Papers by Krzysztof Durka
Impact of Cis–Trans Isomerism on Crystal Packing and Photo-Activity of a Cobalt(III) Room-Temperature Photoswitch
Crystal Growth & Design
TADF Invariant of Host Polarity and Ultralong Fluorescence Lifetimes in a Donor‐Acceptor Emitter Featuring a Hybrid Sulfone‐Triarylboron Acceptor**
Angewandte Chemie
CCDC 1857286: Experimental Crystal Structure Determination
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
CCDC 1449069: Experimental Crystal Structure Determination
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
CCDC 1449066: Experimental Crystal Structure Determination
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
CCDC 1521860: Experimental Crystal Structure Determination
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
High-resolution X-ray diffraction data set for model odbaHQ complex (March 2017 Warsaw)
High-resolution X-ray diffraction data set of luminescent ortho-phenylenediboronic acid 8-hydroxy... more High-resolution X-ray diffraction data set of luminescent ortho-phenylenediboronic acid 8-hydroxyquinoline adduct crystals collected in Warsaw, Poland, for charge density analysis. Additionally, crystallographic information files (CIFs), JANA (Z. Kristallogr. 2014, 229, 345-352) and MOPRO (J. Appl. Cryst. 2005, 38, 38-54) programs refinement results are provided with associated files.
CCDC 1435655: Experimental Crystal Structure Determination
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
CCDC 1025401: Experimental Crystal Structure Determination
An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
Expedient Synthesis of Oxaboracyclic Compounds Based on Naphthalene and Biphenyl Backbone and Phase‐Dependent Luminescence of their Chelate Complexes
Chemistry – A European Journal, 2022
The approach to a series of six- and seven-membered oxaboraheterocycles based on naphthalene or b... more The approach to a series of six- and seven-membered oxaboraheterocycles based on naphthalene or biphenyl backbones was developed. The key synthetic step involved Br/Li exchange in respective potassium (bromoaryl)trifluoroborates followed by quenching with selected electrophiles (CO 2 , DMF, Me 2 Si(H)Cl) and hydrolytic workup. Two ring-expanded benzoxaborole congeners were obtained by an additional reduction step with LiAlH 4 or NaBH 4 . The obtained boracyclic compounds were characterized in detail by NMR spectroscopy and single-crystal X-ray diffraction. Specifically, biphenyl-based systems show dynamic behaviour interpreted in terms of inversion of non-planar 7-membered boraheterocycles. The acidity of the obtained compounds varies very strongly ( p K a ranges from 3.1-9.6) depending on their structure. Due to the enhanced boron Lewis acidity, selected compounds were used as a basis for luminescent complexes with 8-hydroxyquinoline. A strong phase-dependent variation of emission band maximum (480-527 nm) and photoluminescence quantum yield (10-95%) was observed, which was rationalized in terms of specific aggregation effects.
Excited-state photodynamics of pyrene-containing boronated dyes
Dyes and Pigments, 2021
Design of solvatomorphic structures based on polyboronated tetraphenyladamantane molecular tecton
CrystEngComm, 2021
A series of solvatomorphic structures of tetrakis(4-dihydroxyborylphenyl)adamantane, 1, have been... more A series of solvatomorphic structures of tetrakis(4-dihydroxyborylphenyl)adamantane, 1, have been prepared and analyzed by single crystal X-ray diffraction methods. Tetraboronated adamantane represents valuable scaffold for the formation of various supramolecular...
Boronate Covalent and Hybrid Organic Frameworks Featuring P III and P=O Lewis Base Sites
Chemistry – A European Journal, 2020
Invited for the cover of this issue is Sergiusz Luliński and his co‐workers from Warsaw Universit... more Invited for the cover of this issue is Sergiusz Luliński and his co‐workers from Warsaw University of Technology and University of Warsaw. The image depicts a journey through the interior of the porous Covalent Organic Framework containing phosphorus and boron centres with carbon dioxygen trapped inside an imagined cave. Read the full text of the article at 10.1002/chem.202001960.
Ground-State Charge-Density Distribution in a Crystal of the Luminescent ortho-Phenylenediboronic Acid Complex with 8-Hydroxyquinoline
The Journal of Physical Chemistry A, 2018
This contribution is devoted to the first electron density studies of a luminescent oxyquinolinat... more This contribution is devoted to the first electron density studies of a luminescent oxyquinolinato boron complex in the solid state. ortho-Phenylenediboronic acid mixed with 8-hydroxyquinoline in dioxane forms high-quality single crystals via slow solvent evaporation, which allows successful high resolution data collection (sin θ/λ = 1.2 Å-1) and charge density distribution modeling. Particular attention has been paid to the boron-oxygen fragment connecting the two parts of the complex, and to the solvent species exhibiting anharmonic thermal motion. The experiment and theory compared rather well in terms of atomic charges and volumes, except for the boron centers. Boron atoms, as expected, constitute the most electron-deficient species in the complex molecule, whereas the neighboring oxygen and carbon atoms are the most significantly negatively charged ones. This part of the molecule appears to be very much involved in the charge transfer occurring between the acid fragment and oxyquinoline moiety leading to the observed fluorescence, as supported by the time-dependent density functional theory (TDDFT) results and the generated transition density maps. TDDFT calculations indicated that p-type atomic orbitals contributing to the HOMO-1, HOMO, and LUMO play the major role in the lowest energy transitions, and enabled further comparison with the charge density features, which is discussed in details. Furthermore, the results confirmed the known fact the Q ligand character is most important for the spectroscopic properties of this class of complexes.
Antimicrobial and KPC/AmpC inhibitory activity of functionalized benzosiloxaboroles
European Journal of Medicinal Chemistry, 2019
A series of 22 benzosiloxaboroles, silicon analogues of strong antimicrobial agents - benzoxaboro... more A series of 22 benzosiloxaboroles, silicon analogues of strong antimicrobial agents - benzoxaboroles, have been synthesized and tested against β-lactamases KPC- and pAmpC-producing strains of Gram-negative rods. Comprehensive structural-property relationship studies supported by molecular modelling as well as biological studies reveal that 6-B(OH)2-substituted derivative 27 strongly inhibits the activity of cephalosporinases (chromosomally encoded AmpC and plasmid encoded CMY-2) and KPC carbapenemases. It also shows strong ability to inhibit growth of the strains producing KPC-3 when combined with meropenem. In addition, halogen-substituted (mono-, di- or tetra-) benzosiloxaboroles demonstrate high antifungal activity (MIC 1.56-6.25 mg/L) against C. tropicalis, C. guilliermondii and S. cerevisiae. The highest activity against pathogenic yeasts (C. albicans, C. krusei and C. parapsilosis - MICs 12.5 mg/L) and against Gram-positive cocci (S. aureus and E. faecalis - 6.25 mg/L and 25 mg/L respectively) was displayed by 6,7-dichloro-substituted benzosiloxaborole. The studied systems exhibit low cytotoxity toward human lung fibroblasts.
New class of easily-synthesisable and modifiable organic materials for applications in luminescent devices
Dyes and Pigments, 2017
Abstract New class of cheap, easily-synthesisable and modifiable organic luminescent materials is... more Abstract New class of cheap, easily-synthesisable and modifiable organic luminescent materials is presented. 1,2-phenylenediboronic acid reacts with 8-hydroxyquinoline in high yield, both in solution and under mechanochemical conditions, and forms a brightly luminescent complex (emission maxima c.a. 500 nm (solid state) – 525 nm (solution)). This very first luminescent boronic 8-oxoquinoline complex exhibits emission lifetime of ns order, which, together with the DFT results, indicates a singlet-singlet origin of the fluorescence. The emission quantum yield, determined in acetonitrile is significant ( c.a. 15%) and may be increased by choice of solvent. Additionally, the impact of the enhanced Lewis acidity of boron centres in the acid moiety was investigated on a series of the fluoro derivatives of 1,2-phenylenediboronic acid reacted with 8-hydroxyquinoline. In general, the mono -oxyquinolinato complex is preferably formed, however, in the case of the tetra -fluorinated acid a doubly-coordinated complex is stable and favourable. Interestingly, all of the fluorinated complexes exhibit highly comparable luminescent properties to the parent complex. Importantly, the obtained complexes appeared to be electroluminescent, thus a working OLED was successfully produced and tested.
Hybrid Triazine-Boron Two-Dimensional Covalent Organic Frameworks: Synthesis, Characterization, and DFT Approach to Layer Interaction Energies
ACS Applied Materials & Interfaces, 2017
The conversion of 2,4,6-tris(4'-bromophenyl)-1,3,5-triazine to the respective triboronic ... more The conversion of 2,4,6-tris(4'-bromophenyl)-1,3,5-triazine to the respective triboronic acid was successfully accomplished by a simple triple Br/Li exchange followed by boronation. Further dehydrative condensation reactions with 2,3,6,7,10,11-hexahydroxytriphenylene or 2,3,6,7-tetrahydroxy-9,10-dilalkylanthracenes (R = Me, Et) resulted in materials featuring good porosity and sorption properties with the nitrogen uptake exceeding 500 cm3/g (STP) and SBET up to 1267 m2/g (T = 77.2 K). In addition, simple dehydration of this compound was employed for the preparation of a hybrid 2D COF composed of triazine, boroxine, and benzene rings. The formation of materials was confirmed by the IR analysis and NMR studies on water-decomposed samples. All obtained COFs exhibit high thermal stability with decomposition temperatures in the range of 400-600 °C. They also show quite different morphology ranging from regular 0.5-4 μm spherical and ellipsoidal clusters to 5-12 μm bent rodlike particles. The PXRD studies supported by periodic DFT modeling in Crystal09 package revealed the formation of crystalline 2D honeycomb-type lattices with eclipsed stacking models. In addition, the differences between boroxine-triazine material and related COF-1 and CTF-1 structures were investigated by comparing layer interaction energies, work function values as well as atomic charges and electrostatic potential maps plotted on the electron density surfaces. It demonstrates that the interactions between layers are enhanced by the stacking of triazine and boroxine rings. Finally, we have investigated the upper limit to space accessible volume using a procrystal electron density approach.
Visible-light-promoted alkylation of unsaturated MIDA boronates using Ru(bpy) 3 Cl 2 as the photoredox catalyst
Tetrahedron Letters, 2017
The development of a visible light-mediated atom transfer radical addition (ATRA) of perfluoroalk... more The development of a visible light-mediated atom transfer radical addition (ATRA) of perfluoroalkyl iodides to ethynyl-, vinyl- and allyl-MIDA boronates using the reductive and oxidative quenching of [Ru(bpy)3]Cl2 is described. Using an operationally simple and mild protocol, the corresponding MIDA boronates containing perfluoroalkyl groups were obtained in moderate to high yields. The structures of three products were confirmed by single crystal X-ray diffraction studies.
Synthesis and Transformations of Functionalized Benzosiloxaboroles
European Journal of Organic Chemistry, 2017
The synthesis and characterization of a series of fluorinated benzosiloxaboroles bearing the synt... more The synthesis and characterization of a series of fluorinated benzosiloxaboroles bearing the synthetically useful formyl and cyano groups is reported. These compounds have been obtained by multistep syntheses starting with simple halogenated benzenes. The general synthetic protocol was based on the generation ortho-boronated aryldimethylsilanes which undergo dehydrogenative cyclization upon hydrolytic workup due to the activation of the Si-H bond by the adjacent boronic group. In some cases the synergy of adjacent boron- and silicon-based functionalities resulted in an unexpected hydrosilylation of CHO group under mild aqueous conditions. The reduction of a benzosiloxaborole derivative bearing the formyl at the ortho position with respect to the boron atom resulted in the structural transformation reflecting the higher stability of the carboxaborole heterocycle with respect to its silicon counterpart. Thus, a unique heterocyclic system featuring a central 10-membered ring comprising two borasiloxane linkages was isolated.
Acta Crystallographica Section A Foundations and Advances, 2015
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Papers by Krzysztof Durka