dr hab. inż. Ewa Wagner-Wysiecka
Employment
- Head of Department at Department of Chemistry and Technology of Functional Materials
- Associate professor at Department of Chemistry and Technology of Functional Materials
Publications
Filters
total: 68
Catalog Publications
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Azo group(s) in selected macrocyclic compounds
PublicationAzobenzene 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
PublicationZsyntezowano 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
PublicationMicrowave-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
PublicationOtrzymano 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
PublicationOpisano 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)
PublicationNatural 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
PublicationNew 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
PublicationThe 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
PublicationThe 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
Publicationα,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
PublicationMetal 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
PublicationThe 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
PublicationDiazocrowns 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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Naphthyl-vs. anthrylpyridine-2,6-dicarboxamides in cation binding studies. Synthesis and spectroscopic properties
PublicationPyridine-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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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
PublicationThis 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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Simple colorimetric copper(II) sensor – spectral characterization and possible applications
PublicationNew 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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Iron(III)-selective materials based on a catechol-bearing amide for optical sensing
PublicationThe 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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pH-tunable equilibria in azocrown ethers with histidine moieties
PublicationEtery 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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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
PublicationThe 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
PublicationThe 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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Minute and diverse in fossil sticky stuff: Tanytarsini (Diptera: Chironomidae) from early Eocene Indian Cambay amber
PublicationWe 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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1,3,4-Thiadiazole-based diamides: Synthesis and complexation properties
PublicationAromatic 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
PublicationThe 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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Novel Diazocrowns with Pyrrole Residue as Lead(II) Colorimetric Probes
PublicationNovel 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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Ion recognition properties of new pyridine-2,6-dicarboxamide bearing propeller-like pendant residues: multi-spectroscopic approach
PublicationThe 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
PublicationThe 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?
PublicationNew 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
PublicationThe 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
PublicationIn 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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Nowe makrocykliczne chromojonofory, synteza i charakterystyka oddziaływań z kationami.**2002, 104 s. 77 rys. 13 tab. bibliogr. 129 poz. maszyn.
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Azo macrocyclic compounds.
PublicationArtykuł przeglądowy omawiający głównie syntezę i właściwości związków makrocyklicznych takich jak: etery koronowe, kryptandy, kaliksareny i inne, które połączono z fragmentem zawierającym resztę azobenzenową lub jej analogi. Artykuł napisany został w oparciu o prace własne autorów z lat 1992-2001 oraz na podstawie literatury obcej zebranej na podstawie Chemical Abstracts z lat 1990-2001.
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Metallochromic crown ether analogs bearing aromatic residues and azo groupings
PublicationPraca zawiera przegląd syntezowanych, różnych chromogenicznych związków koronowych, zawierających oprócz dwóch grup azowych i łańcucha polieterowego fragmenty heterocykliczne. Porównano właściwości otrzymanych związków w zależności od obecności heteroatomów w pierścieniu makrocyklicznym oraz różnego podstawienia cząsteczki heterocykliczej.
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Azo macrocyclic compounds
PublicationArtykuł przeglądowy dotyczący azozwiązków makrocyklicznych
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Synthesis and properties of azobenzocrown ethers with pi-electron donor, or pi-electron donor and pi-electron acceptor group(s) on benzene rings
PublicationZsyntezowano nowe etery azobenzokoronowe o różnej wielkości makropierścienia i z różnymi podstawnikami w resztach benzenowych. Korony te posiadają w pierścieniach benzenowych, w pozycji para do grupy azo grupy funkcyjne o charakterze π-elektronodonorowym lub π-elektronoakceptorowym. Zbadano zdolność kompleksowania jonów metali przez te korony, w roztworze, metodą spektrofotometrii UV-vis. Ustalono strukturę 19-członowego eteru...
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Chromogenic Azocrown Ethers with Peripheral Alkyl, Alkoxy, Hydroxyl or Di-methylamino Group.
PublicationOtrzymano nowe pochodne azobenzenowych eterów koronowych. Są to związki z grupą alkilową, alkoksylową, hydroksylową lub dimetyloaminową w reszcie (resztach) aromatycznej jako boczny podstawnik. Badano ich właściwości jako jonoforów w membranowych elektrodach jonoselektywnych oraz właściwości chromo-jonoforowe w roztworach. Badano kompleksowanie jonów metali, w acetonitrylu,przez te korony, metodą spektrofotometryczną. Badano...
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Chromogenic Macrocyclic Derivatives of Azoles - Synthesis and Properties
PublicationOpisano syntezę makrocyklicznych azokoron zawierających resztę pirolu i imi-dazolu w makropierścieniu. Zbadano zdolność kompleksowania kationów metaliprzez otrzymane związki makrocykliczne przy pomocy spektrofotometrii UV-Visw acetonitrylu. Zbadano także właściwości jonoforowe związków w membranowychelektrodach jonoselektywnych. Ustalono strukturę krystalograficzną 18-czło-nowej pochodnej pirolu.
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Characterization of Small Azocrown Ether Stereoisomers.
PublicationWyizolowano i zbadano metodą X-ray, 1H NMR i UV-Vis trwałe izomery E i Z 10-członowej azokorony. Ich struktura w stanie stałym świadczy o naprężonej konformacji w przypadku izomeru trans i nie naprężonej dla izomeru cis. Jest to efektem sprzężenia p grupy azowej z benzenem i naprężenia sterycznego konformacji cząsteczki.
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A Chemical Recognition Element for Lithium Ions Based on Optical Electronic Absorption.
PublicationOtrzymano próbki kserożeli techniką zol-żel. Otrzymane materiały zastosowano do konstrukcji czujników optycznych. Rolę elementu rozpoznającego w uzyskanych próbkach pełnią chromogeniczne etery koronowe zawierające w makro pierścieniu dwie grupy azowe oraz resztę fenolu. W obecności soli metali I grupy układ u okresowego obserwowano zmiany w widmach absorpcyjnych. Dla matrycy zawierającej jako materiał czujnikowy 21-członową...
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Fluorescence of p-hydroxyazobenzocrowns – Tautomeric equilibrium effect
PublicationThe spectroscopic properties of a series of para-hydroxyazobenzocrowns, including three novel compounds, were investigated using UV–Vis absorption and emission spectroscopy. This study presents, for the first time, determined quantum yield (QY) values for macrocycles of this category, ranging between 0.122 and 0.195. The highest values were obtained for crowns bearing two phenyl substituents in benzene rings. The impact of aromatic...
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Macrocyclic derivatives of imidazole as chromoionophores for bismuth(III)/lead(II) pair
Publication18-membered diazomacrocycles with imidazole or 4-methylimidazole residue as a part of macrocycle were used as chromoionophores in bismuth(III) and lead(II) dual selective optodes for the first time. Cellulose triacetate membranes doped with macrocyclic chromoionophores are bismuth(III) and lead(II) selective with color change from orange/red to different shades of blue and violet, respectively. Results obtained for model and real...
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Recognition and sensing of anions
PublicationMolecular 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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Diagnostyczne pasma IRS po modyfikacji bursztynu
PublicationBadania 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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Goitszyt zasługuje na nazwę...Rzecz o nomenklaturze mineralogicznej żywic naturalnych
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Anion recognition by n,n'-diarylalkanediamides
PublicationThe 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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Bis(azobenzocrown ether)s-synthesis
PublicationSyntezowano 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
PublicationAmides 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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Pyrrole azocrown ethers - synthesis, crystal structures, and fluorescence properties
PublicationZsyntezowano 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
PublicationChemiczny 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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Determination of the chemical structure of potencial organic impurities occuring in the drug substance opopramol
PublicationThe 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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