dr hab. inż. Ewa Wagner-Wysiecka
Zatrudnienie
- Kierownik katedry w Katedra Chemii i Technologii Materiałów Funkcjonalnych
- Profesor uczelni w Katedra Chemii i Technologii Materiałów Funkcjonalnych
Publikacje
Filtry
wszystkich: 68
Katalog Publikacji
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Azo group(s) in selected macrocyclic compounds
PublikacjaAzobenzene derivatives due to their photo- and electroactive properties are an important group of compounds finding applications in diverse fields. Due to the possibility of controlling the trans–cis isomerization, azo-bearing structures are ideal building blocks for development of e.g. nanomaterials, smart polymers, molecular containers, photoswitches, and sensors. Important role play also macrocyclic compounds well known for...
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Anion recognition by α-arylazo-N-confused calix[4]pyrroles
PublikacjaZsyntezowano nowe azowe pochodne N-odwróconych kaliks[4]piroli na drodze sprzęgania z różnymi solami arylodiazoniowymi. Zbadano zdolność kompleksowania anionów w chlorku metylenu oraz w acetonitrylu przez otrzymane związki z zastosowaniem spektrofotometrii UV-Vis.
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A review of amide bond formation in microwave organic synthesis
PublikacjaMicrowave-Assisted Organic Synthesis (MAOS) is one of the most current trends in organic chemistry. Herein, both the most popular and new approaches in microwave-syntheses of very important linkage in Nature - amide bond - are overviewed and compared with conventional synthetic routes.
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Pyrrole azocrown ethers. Synthesis, complexation, selective lead transport and ion-selective membrane electrode studies
PublikacjaOtrzymano nowe, 21-członowe, lipofilowe etery koronowe z jednostką pirolową i dwoma grupami azowymi jako składowymi makrocyklu. Właściwości kompleksujące tych nowych oraz dwóch wcześniej otrzymanych makrocykli zbadano w acetonitrylu. Ligandy te zostały użyte jako jonofory w badaniach konkurencyjnego transportu równomolowej mieszaniny jonów metali: Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Ag2+, Pb2+ w układzie woda(pH 4.9)/chloroform/woda(pH...
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4-Hexylresorcinol-derived hydroxyazobenzocrown ethers as chromoionophores
PublikacjaOpisano syntezę nowych chromogenicznych azobenzokoron z grupą hydroksylową w pozycji para w stosunku do grupy azowej. Zdolność kompleksowania wybranych kationów litowców i berylowców przez otrzymane barwne związki makrocykliczne zbadano w acetonitrylu przy pomocy spektroskopii UV-Vis.
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Mid-infrared spectroscopy for characterization of Baltic amber (succinite)
PublikacjaNatural Baltic amber (succinite) is the most appreciated fossil resin of the rich cultural traditions dating back to prehistoric times. Its unequivocal identification is extremely important in many branches of science and trades including archeology, paleontology, chemistry and finally mineralogical and gemological societies. Current methods of modification of natural succinite are more and more sophisticated making the identification...
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Functionalized azobenzocrown ethers as sensor materials—The synthesis and ion binding properties
PublikacjaNew 13- and 16-membered azobenzocrown ethers with aromatic amino, amide, ether–ester or ether–amide residue in para position to an azo moiety were obtained. Acid–base properties and ion binding ability of the colored compounds were studied by spectroscopic methods: UV–vis, fluorimetry and 1H NMR spectroscopy. Selected azobenzocrowns were tested as ionophores in ion-selective membrane electrodes (ISEs) – classic and miniature all...
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Chromogenic amides of pyridine-2,6-dicarboxylic acid as anion receptors
PublikacjaThe synthesis of simple, chromogenic pyridine-2,6-dicarboxylic acid amides, derivates of isomeric nitroanilines and aminonitrophenols, and their ion binding properties are described. The ligands' response to ionic species was examined by naked eye and was studied with the use of UV-Vis spectroscopy in DMSO and its mixture with water. The effect of the localisation and the type of the substituents in aromatic rings were discussed....
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Rearrangement of azoxybenzocrowns into chromophoric hydroxyazobenzocrowns and the use of hydroxyazobenzocrowns for the synthesis of ionophoric biscrown compounds
PublikacjaThe Wallach rearrangement was used as a method for preparing p-hydroxyazobenzocrown ethers starting from different azoxybenzocrowns as substrates. Synthesis of a series of p-hydroxyazobenzocrowns under modified conditions and characterization of the obtained products are presented. o-Hydroxyazobenzocrowns were identified among the products of the photochemical rearrangement of azoxybenzocrowns. Novel biscrowns were synthesized...
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Salicylaldimine-based receptor as a material for iron(III) selective optical sensing
Publikacjaα,α-Bis(salicylimino)-m-xylene (L) was prepared using both conventional and microwave-assisted procedure. The compound exhibits ability to colorimetric recognition of iron(III) ions in aqueous environment, what is shown by significant color change from yellow to purple. In DMSO : water (9:1 v/v) solvent system receptor creates with iron(III) cations complexes of 2:1 stoichiometry (L:Fe3+) with stability constant (log K) 7.54±0.21....
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Cation sensing by diphenyl-azobenzocrowns
PublikacjaMetal cations complexation and proton binding by 13- and 16-membered diphenyl-azobenzocrowns and diphenyl-hydroxyazobenzocrowns were studied in acetonitrile using spectroscopic methods: UV–vis spectroscopy, spectrofluorimetry, and 1H NMR spectroscopy. Phenyl moieties in benzene rings were found to affect binding strength alkali and alkaline earth metal cations and hydrogen ion, and affect tautomeric equilibrium of hydroxyazobenzocrowns....
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Photoresponsive, amide-based derivative of embonic acid for anion recognition
PublikacjaThe synthesis and ion-binding properties of amide-based derivative of embonic acid andp-aminoazobenzenewere described. The new compound was characterized by X-ray structural analysis and spectroscopic methods.Ligand interacts in acetonitrile with Y-shaped anions (benzoates and acetates) and dihydrogen phosphatesforming complexes of 1:1 stoichiometry. In more polar DMSO the complexes stoichiometry changes to 2:1(L:anion). Light-inducedtranstocisisomerization...
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Pyrrole bearing diazocrowns: Selective chromoionophores for lead(II) optical sensing
PublikacjaDiazocrowns of 18-, 21- and 23-membered rings with pyrrole residue as a part of macrocycle were for the first time used as chromoionophores in lead(II) selective optodes. Sensing properties of optodes depend on the type of macrocycle, namely its size and the type of linker: oligoether or hydrocarbon chain. The best results were obtained for optode bearing 18-membered crown with oligoether linker showing linear response range of...
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Golden artefacts, resin figurines, body adhesives and tomb sediments from the pre-Columbian burial site El Caño (Gran Coclé, Panamá): tracing organic contents using molecular archaeometry
PublikacjaThis research aimed to determine the origin of organic residues from funerary contexts in the El Ca~no settlement (Gran Cocl�e area, Panam�a, Central America) by means of multiple molecular probing techniques (GC-MS of organic solvent extracts and pyrolysis-GC-MS, THM-GC-MS and FTIR of solid samples). The samples include particles of precious resin figurines, fillings of golden objects, tomb sediments, plant exudates from extant...
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Naphthyl-vs. anthrylpyridine-2,6-dicarboxamides in cation binding studies. Synthesis and spectroscopic properties
PublikacjaPyridine-2,6-carboxamides bearing - or -naphthyl- and - or -anthryl- residues were prepared using simple method from pyridine-2,6-carboxylic acid dichloride and the respective aromatic amines. For the obtained receptors selective binding of lead(II), and copper(II) was found. Ion-receptor interactions were studied using UV-vis spectroscopy, spectrofluorimetry, 1H NMR, and FTIR spectroscopy. The reversible lead(II) and copper(II)...
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Simple colorimetric copper(II) sensor – spectral characterization and possible applications
PublikacjaNew o-hydroxyazocompound L bearing pyrrole residue was obtained in the simple synthetic protocol. The structure of L was confirmed and analyzed by X-ray diffraction. It was found that new chemosensor can be successfully used as copper(II) selective spectrophotometric regent in solution and can be also applied for the preparation of sensing materials generating selective color signal upon interaction with copper(II). Selective colorimetric...
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pH-tunable equilibria in azocrown ethers with histidine moieties
PublikacjaEtery koronowe posiadające elektro- i fotoaktywne reszty azowe oraz ugrupowania z ruchliwymi protonami jak w grupie COOH histydyny charakteryzują się unikalnym, zależnym od pH, efektem stymulowania pozornej obecności/nieobecności ugrupowania azowego. Obserwowane różnice właściwości elektrochemicznych eterów azokoronowych z resztą N-acetylohistydyny lub resztami imidazolu uwidaczniają się przebiegiem chemicznej redukcji w silnie...
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Minute and diverse in fossil sticky stuff: Tanytarsini (Diptera: Chironomidae) from early Eocene Indian Cambay amber
PublikacjaWe here present a pioneering systematic review of fossil dipterans of the tribe Tanytarsini (family Chironomidae) discovered in Indian amber from Cambay. The specimens examined belong to five species: Gujaratomyia miripes, Stempellina stebneri sp. nov., Stempellinella pollex sp. nov., Tanytarsus forfex sp. nov. and Tanytarsus ramus sp. nov., which are described. All species belong to the oldest known Tanytarsini and come from the...
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Iron(III)-selective materials based on a catechol-bearing amide for optical sensing
PublikacjaThe synthesis and ion-binding properties of a new amide L derived from 3,4-dihydroxybenzoic acid are described. Due to the presence of a catechol unit, the compound interacts selectively with iron(III) in organic solvent (dimethyl sulfoxide, DMSO) to produce a color change from pale yellow to green. The incorporation of the ligand L into polymeric matrices or its encapsulation into surfactant-based spheres enables analyte detection...
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Synthesis of thiol derivatives of azobenzocrown ethers. The preliminary studies on recognition of alkali metal ions by gold nanoparticles functionalized with azobenzocrown and lipoic acid
PublikacjaThe article presents the synthesis of novel 13- and 16-membered azobenzocrown derivatives with peripheral thiol moieties and preliminary studies assessing their possible application in plasmonic sensors based on gold nanoparticles. The effect of the length of the chain connecting the macrocycle with the thiol group and the effect of the presence of the additional functional compound,...
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Photochemical Rearrangement of a 19-Membered Azoxybenzocrown: Products and their Properties
PublikacjaThe preparation and characterization of products of the chemical and photochemical rearrangements of a 19-membered o,o'-azoxybenzocrown were presented. In photochemical rearrangement, besides expected product i.e. 19-membered o-hydroxy-o,o'-azobenzocrown (19-o-OH), obtained under defined conditions with 75% yield, also other macrocyclic products were isolated and identified, namely: 19-membered p-hydroxy-o,o'-azobenzocrown (19-p-OH),...
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Novel Diazocrowns with Pyrrole Residue as Lead(II) Colorimetric Probes
PublikacjaNovel 18- and 23-membered diazomacrocycles were obtained with satisfactory yields by diazocoupling of aromatic diamines with pyrrole in reactions carried under high dilution conditions. X-ray structure of macrocycle bearing five carbon atoms linkage was determined and described. Compounds were characterized as chromogenic heavy metal ions receptors. Selective color and spectral response for lead(II) was found in acetonitrile and...
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1,3,4-Thiadiazole-based diamides: Synthesis and complexation properties
PublikacjaAromatic diamides, derivative of 2,6-pyridinedicarboxylic acid and isophthalic acid, bearing 1,3,4-thiadiazole residue were prepared with satisfactory yields in conventional procedures and microwave stimulated reactions. X-ray structure of N,N-bis (1,3,4-thiadiazol-2-yl)-2,6-pyridinedicarboxamide (2) DMSO solvate (2DMSO) was described. Selective zinc(II), lanthanum(III), terbium(III) and L-tyrosine recognition was found for N,N-bis(1,3,4-thiadiazol-2-yl)-2,6-pyridinedicarboxamide...
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Anion binding by p-aminoazobenzene-derived aromatic amides: spectroscopic and electrochemical studies
PublikacjaThe synthesis and complexing properties of p-aminoazobenzene-derived mono-, bis-, and trisamides were described. Ligands 3 and 4 bind anions, including fluorides, chlorides, bromides, acetates, benzoates, dihydrogen phosphates, hydrogen sulfates, and p-toluenesulfonates, in chloroform forming 1 : 1 complexes. The highest value of stability constant was evaluated for the 4-F− complex (log K = 5.63 ± 0.21). On the basis of 1H NMR,...
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Ion recognition properties of new pyridine-2,6-dicarboxamide bearing propeller-like pendant residues: multi-spectroscopic approach
PublikacjaThe synthesis and ion binding properties of new amide derived from propeller-like tris(2-pyridyl)amine and 2,6-pyridinedicarboxylic acid chloride were described. Amide binds divalent metal cations: copper(II), nickel(II), zinc(II), and lead(II) in acetonitrile. In acetonitrile:water mixture (9:1 v/v) amide interacts only with copper(II) and nickel(II) cations forming complexes of 1:1 stoichiometry. It was found that the introduction...
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Products of Photo- and Thermochemical Rearrangement of 19-Membered di-tert-Butyl-Azoxybenzocrown
PublikacjaThe preparation and characterization of products of the photochemical and thermochemical rearrangements of 19-membered azoxybenzocrowns with two, bulky, tert-butyl substituents in benzene rings in the para positions to oligooxyethylene fragments (meta positions to azoxy group, i.e., t-Bu-19-Azo-O have been presented. In photochemical rearrangement, two colored typical products were expected, i.e., 19-membered o-hydroxy-m,m′-di-tert-butyl-azobenzocrown...
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Do Phenyl Substituents Affect the Properties of Azobenzocrown Derivatives?
PublikacjaNew products of photo- and thermal rearrangements of 19-membered azoxybenzocrown with phenyl substituents in benzene rings in the para positions to oligooxyethylene fragments are characterized. The yields of photochemical transformations depend on the solvent. Para-hydroxyazocrown is formed with yields over 50% in propan-2-ol. Ortho-hydroxyazobenzocrown is obtained with yields up to 70% in toluene/acetic acid mixture. Macrocyclic...
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Provenance studies on Late Neolithic amber ornaments from North-East Poland
PublikacjaThe area of North-East Poland was in prehistory, and still is today, an area with easy access to amber as a raw material, as is evidenced in part by numerous Late Neolithic (3rd millennium) amber workshops located in the Gulf of Gdańsk and Żuławy Wiślane (Vistula Fens). Given this fact, it is surprising that only a few finished amber products have been recovered from this area. Among them are unique ornaments from the Late Neolithic...
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Correction to: Azo group(s) in selected macrocyclic compounds
PublikacjaIn the original publication of the article, a part of Scheme 12 was missed. The correct version of Scheme 12 was provided in this correction article. The original article has also been corrected.
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Azomacrocyclic derivatives of imidazole: synthesis, structure, and metal ion complexation properties
PublikacjaOtrzymano nowe azokorony zawierające resztę imidazolu w makropierścieniu. Na drodze sprzęgania z solami diazoniowymiotrzymano pochodne imidazolu 2-metylo, 4-metylo oraz 4-fenyloimidazolu. Synteza była prowadzona w warunkach wysokiego ciśnienia. Dla 21-członowej pochodnej 4-metyloimidazolu określono strukturę jej adduktu z wodą przy pomocy metod rentgenograficznych.Zdolność kompleksowania jonów metali badano spektrofotometrycznie...
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Optical recognition elements. Macrocyclic imidazole chromoionophores entrapped in silica xerogel
PublikacjaNowe chromojonofory zawierające fragment eteru koronowego i resztę azolu zostały unieruchomione w krzemionkowej matrycy żelowej metodą zol-żel i zbadane jako optyczne elementy rozpoznające kationy Li+,Cs+, Cu2+. Elementy optyczne oparte na 21-członowych pochodnych imidazolu i 4-metyloimidazolu rozpoznawały jony Li+ w roztworze wodnym. Wyznaczono parametry g i A na podstawie badań EPR dla kompleksów 18-członowej i 21-członowej pochodnej...
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The synthesis, x-ray structure and metal cation complexation properties of colored crown with two heterocyclic residues as a part of macrocycle
PublikacjaZsyntezowano nowy eter koronowy zawierający ugrupowanie azowe, resztę pirolu i pirydyny w pierścieniu makrocyklicznym. Badano zdolność kompleksowania kationów metali w acetonitrylu oraz mieszaninę acetonitryl-woda. Do pomiarów wykorzystano spektrofotometrię UV-Vis. Ustalono strukturę krystalograficzną otrzymanego związku.
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Goitszyt zasługuje na nazwę...Rzecz o nomenklaturze mineralogicznej żywic naturalnych
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Bis(azobenzocrown ether)s-synthesis
PublikacjaSyntezowano nowe związki bisazobenzokoronowe różniące się wielkością makropierścienia i długością łańcucha łączącego oba pierścienie makrocykliczne. Związki te wykorzystano jako jonofory w membranach klasycznych i miniaturowych elektrod jonoselektywnych. Przeprowadzono również badania dotyczące kompleksowania soli litowców i berylowców w roztworze acetonitrylowym z wykorzystaniem spektrofotometrii UV-VIS oraz zbadano strukturę...
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Synthesis of amides under microwave irradiation
PublikacjaAmides belong to the most important carboxylic acid derivatives. They are constituents of natural compounds like peptides and proteins. They found applications in many branches of science and industry, especially in pharmaceutical and polymer science. Conventional procedures for amide preparation involve reaction between amine and carboxylic acid or their more active derivatives such as acid chlorides, acid anhydrides or esters....
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Anion recognition by n,n'-diarylalkanediamides
PublikacjaThe preparation of N,N'-diarylalkanediamides from respective aliphatic dicarboxylic acidesand 4-nitroaniline via microwave-promoted reactions is presented. The most positive effect of microwave irradiation was observed for N,N'-bis(4-nitrophenyl)butanediamide. Anion binding studies on the obtained diamides were carried out in DMSO and acetonitrile using UV-vis and 1H NMR spectroscopy. A mechanism for selective fluoride recognition...
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Determination of the chemical structure of potential organic impurities occurring in drug substance opipramol
PublikacjaThe tricyclic antipsychotic and antidepressant drug opipramol (opipramole) was examined with regard to the chemical structure of its organic impurities. Impurities were isolated from the technical product by chromatographic methods and their chemical structures were established by 1H NMR, MS and FTIR and further confirmed by comparison with commercially available products or with products obtained by independent synthesis, and...
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Optical recognition elements: macrocyclic imidazole chromoionophores entrapped in silica xerogel
PublikacjaMaterials containing new chromoionophores consisting of crown residue and azole moiety as partsof macrocycles were encapsulated by the sol-gel procedure in silica xerogel matrices and proposed aschemical recognition elements especially for such metal ions as Li+, Cs+ and Cu2+. Action of these recognition elements is in principle based on changes of reflectance. The recognition elements containing 21-membered chromogenic...
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Chromogenic macrocyclic derivatives of azoles - synthesis and properties,
PublikacjaNew azocrown ethers comprising imidazoles in the macrocycle have been synthesized. Imidazole, 2-methyl-, 4-methyl-, and 4-phenylimidazole were incorporated to form macrocyclic units by coupling with the appropriate bis-diazonium salts. The syntheseswere performed under high dilution conditions. The X-ray structure of a water adduct of the 21-membered crown ether derivative of 4-methylimidazole 8 has been solved. Metal...
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pH -Tunable equilibria in azocrown ethers with histidine moieties, Bioelectrochemistry
PublikacjaThe crown ethers with electro- and photoactive azo moieties containing substituents with mobile protons such as in the –COOH groups of histidine, show unique effect of pH switched on/off presence of the azo form. The differences observed for the electrochemical behavior of azocrown ethers with N-acetylhistidine and imidazole moieties reveal the interference of a chemical reduction pathway in strongly acidified solutions. This...
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Azomacrocyclic derivatives of imidazole: synthesis, structure, and metal ion complexation properties
PublikacjaNew azocrown ethers comprising imidazoles in the macrocycle have been synthesized. Imidazole, 2-methyl-, 4-methyl-, and 4-phenylimidazole were incorporated to form macrocyclic units by coupling with the appropriate bis-diazonium salts. The syntheseswere performed under high dilution conditions. The X-ray structure of a water adduct of the 21-membered crown ether derivative of 4-methylimidazole 8 has been solved. Metal...
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Determination of the chemical structure of potencial organic impurities occuring in the drug substance opopramol
PublikacjaThe tricyclic antipsychotic and antidepressant drug opipramol was examined with regard to the chemical structure of its organic impurities. Impurities were isolated from the technical product by chromatographic methods and their chemical structures were estabilished by HMNR, MS and FTIR.
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Amber imitations through the eyes of a chemist
PublikacjaBaltic amber imitations division was proposed. Main types of succinite imitations were presented and characterized. Different methods of identification of Baltic amber imitations were presented.
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Pyrrole azocrown ethers - synthesis, crystal structures, and fluorescence properties
PublikacjaZsyntezowano nowe związki makrocykliczne zawierające w makropierścieniu pierścień pirolowy, grupy azowe oraz reszty chromoforowe i fluorescencyjne. Scharakteryzowano strukturę krystaliczną dwóch spośród otrzymanych makrocykli metodą rentgenografii strukturalnej. Stwierdzono, że zaprezentowane pirolowe azokorony to związki czułe i selektywne na jony ołowiu(II) oraz, że mogą być użyte jako chemosensory zarówno w spektroskopii UV-Vis,...
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Preliminary studies comparing the chemical composition of goitschiteand Saxonian succinite = Wstępne badania dotyczące porównania chemicznego składu goitszytu i sukcynitu saksońskiego
PublikacjaChemiczny skład goitszytu i sukcynitu saksońskiego porównano metodą spektroskopową (FTIR). Dalsza analiza została przeprowadzona z ekstraktów niepolarnych za pomocą chromatografii gazowej sprzężonej ze spektrometrią mas (GC-MS). Potwierdzono podobieństwo składu chemicznego bursztynu bitterfeldzkiego i sukcynitu z regionu Morza Bałtyckiego. Substancje zidentyfikowane w ekstrakcie goitszytu mogą sugerować jego genetyczne podobieństwo...
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Metallochromic azocrown ethers incorporating azole residues
PublikacjaZwiązki o charakterze odczynników metalochromowych są szeroko stosowane w chemii analitycznej. Reagenty te zbudowane są zazwyczaj z grupy fenolowej połączonej z ugrupowaniem azowym. Włączenie takiego podstawnika do związków makrocyklicznych spowodowało utworzenie nowej grupy reagentów o charakterze chromojonoforów. Zsyntezowane zostały nowe makrocykliczne chromojonofory zawierające w makropierścieniu grupę fenolową lub azolową....
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Metallochromic azole azomacrocyclic reagents
PublikacjaW artykule opisano syntezę makrocyklicznych azozwiązków zawierających resztę pirolową lub imidazolową. Zbadano zdolność kompleksowania jonów metali w acetonitrylu (spektroskopia UV-Vis). Otrzymane związki przetestowano jako jonofory w membranowych elektrodach jonoselektywnych.
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Diagnostyczne pasma IRS po modyfikacji bursztynu
PublikacjaBadania spektroskopowe naturalnego, modyfikowanego i prasowanego sukcynitu (bursztynu bałtyckiego), przygotowanego w określony sposób, oraz próbek zebranych w trakcie prowadzonych badań, pozwoliły z dużym prawdopodobieństwem wskazać diagnostyczne odcinki widm, pozwalające odróżnić materiał naturalny od substancji poddanych obróbce innej niż mechaniczna. Są to w różny sposób wykształcone pasma (w cm-1) w okolicach: 1642 i 888, 1012...
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Recognition of environmentally important ions
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Recognition and sensing of anions
PublikacjaMolecular ion recognition is one of the most intensively studied areas of supramolecular technology. The reason for this is the essential role that ions play in many biological as well as industrial processes. On the other hand, however, it has been proved that ions can have a negative impact on human health and the environment. For these reasons, it is extremly important to develop rapid and simple methods allowing the determination...
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