0000000000442078

AUTHOR

Kaisa Helttunen

showing 69 related works from this author

Interaction of aminomethylated resorcinarenes with rhodamine B

2009

The interaction of aminomethylated resorcinarenes with a red xanthene dye, rhodamine B, was investigated in chloroform, methanol and chloroform–methanol solutions using UV-vis, NMR and fluorescence spectroscopy. Aminomethylated resorcinarenes 1 and 2 shift the rhodamine B equilibrium from the zwitterion to the lactone form unlike reference compounds 3 and 4, which do not contain tertiary amino groups at the upper rim, giving an example of how supramolecular hosts can influence the equilibrium of rhodamine B isomers.

chemistry.chemical_classificationChloroformSupramolecular chemistryGeneral ChemistryPhotochemistryCatalysisFluorescence spectroscopychemistry.chemical_compoundchemistryXanthene dyeZwitterionMaterials ChemistryRhodamine BMethanolLactoneNew Journal of Chemistry
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Effect of a Rigid Sulfonamide Bond on Molecular Folding: A Case Study

2015

A disulfonamide compound with bulky aromatic side chains was prepared, and its properties as a potential building block for foldamers were evaluated. Two different solvate crystal forms of the compound were identified and compared to the structures of an analogous oligoamide and related disulfonamides. The disulfonamide is unfolded in one of the solvates, whereas in the other one, a loosely folded conformer stabilized by an intramolecular hydrogen bond is found. Density functional calculations indicated that the loosely folded conformer is slightly more stable than its unfolded isomer. The calculations also identified a third, more tightly folded and more extensively hydrogen bonded, confor…

HydrogenStereochemistrychemistry.chemical_elementmolecular foldingkonformeeritorgaaninen synteesiCrystalSide chainmolecular conformersGeneral Materials Sciencemolekyylien laskostuminenta116sulfonamidisidosConformational isomerismX-ray crystallographychemistry.chemical_classificationHydrogen bondsulfonamide bondGeneral Chemistryorganic synthesisCondensed Matter PhysicsSulfonamideFolding (chemistry)chemistryIntramolecular forceröntgenkristallografiaCrystal Growth & Design
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Binding of ion pairs and neutral guests by aryl-extended meso‑p-hydroxyphenyl calix[4]pyrrole : The interplay between three binding sites

2023

An aryl-extended calix[4]pyrrole with four meso‑p-hydroxyphenyl substituents was investigated as a host for chloride, acetate, and benzoate anions. Crystal structures of pyridinium and imidazolium chloride complexes were obtained in which chloride ions are hydrogen bonded exo-cavity to the upper rim hydroxyl groups, and the aromatic cations are bound to the shallow cavity of the host. Furthermore, the calix[4]pyrrole formed a hydrogen bonded dimeric capsule templated by inclusion of adiponitrile guest in the endo-cavity binding site. NMR titrations revealed the preference of the OH groups of the host to bind anionic guests in solution. Benzoate anion had the highest binding constant (4 700 …

Inorganic ChemistryanionitvuorovaikutusOrganic Chemistrycalix[4]pyrroles host-guest systemssupramolekulaarinen kemiamolekyylitanionsSpectroscopysupramolecular chemistryröntgenkristallografiaAnalytical ChemistryX-ray crystallography
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Bifunktionaalisten reagenssien synteesi, ominaisuudet ja sovellukset

2006

biotiiniHABAlinkkeritavidiiniorgaaninen kemiasynteesiproteiinit
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Polymorphism control of an active pharmaceutical ingredient beneath calixarene-based Langmuir monolayers.

2014

This communication demonstrates the possibility to nucleate and grow different crystalline polymorphic forms of gabapentin (GBP) using, as nucleation templates, Langmuir monolayers of an amphiphilic calixarene at different packing densities.

Models MolecularLangmuirCyclohexanecarboxylic AcidsNucleation02 engineering and technology010402 general chemistry01 natural sciencesCatalysisAmphiphileCalixareneMonolayerMaterials ChemistryOrganic chemistryAminesta116gamma-Aminobutyric AcidActive ingredientMolecular StructureChemistryMetals and AlloysGeneral Chemistry021001 nanoscience & nanotechnology0104 chemical sciencesSurfaces Coatings and FilmsElectronic Optical and Magnetic MaterialsChemical engineeringPolymorphism (materials science)Pharmaceutical PreparationsCeramics and CompositesCalixarenesGabapentin0210 nano-technologyChemical communications (Cambridge, England)
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Influence of lower rim C-methyl group on crystal forms and metal complexation of resorcinarene bis-crown-5

2015

C-methyl resorcinarene bis-crown-5 (1) with pendant methyl groups at the lower rim was prepared and crystallized in various solvent mixtures with and without selected metal salts. The crystal structures of two polymorphic forms of unsolvated 1 (1-I and 1-II), three solvates (acetonitrile, chloroform and dichloromethane-methanol), and three metal complexes with silver and cesium salts were obtained. The lower rim methyl groups and the block shape of the host promote crystal packing in brick-wall type assemblies, in which the binding cavities are efficiently filled by the crown bridges. Thus, solvents are found in the interstitial space or coordinated to the crown bridges on top of the cavity…

ChloroformresorcinareneChemistryInorganic chemistryGeneral ChemistryCrystal structureResorcinareneCondensed Matter PhysicsSolventMetalCrystalchemistry.chemical_compoundCrystallographyvisual_artvisual_art.visual_art_mediumGeneral Materials ScienceAcetonitrileta116Methyl group
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Correlating Solution‐ and Solid‐State Structures of Conformationally Flexible Resorcinarenes: Significance of a Sulfonyl Group in Intramolecular Self…

2020

Abstract The synthesis of tetramethoxyresorcinarene podands bearing p‐toluene arms connected by ‐SO3‐ (1) and ‐CH2O‐ (2) linkers is presented herein. In the solid state, the resorcinarene podand 1 forms an intramolecular self‐inclusion complex with the pendant p‐toluene group of a podand arm, whereas the resorcinarene podand 2 does not show self‐inclusion. The conformations of the flexible resorcinarene podands in solution were investigated by variable‐temperature experiments using 1D and 2D NMR spectroscopic techniques as well as by computational methods, including a conformational search and subsequent DFT optimisation of representative structures. The 1H NMR spectra of 1 and 2 at room te…

Supramolecular chemistryself-inclusionCrystal structure010402 general chemistry01 natural sciencessupramolecular chemistryCatalysissupramolekulaarinen kemiasolution structuresMoleculesolution structureX-ray crystallographySulfonylchemistry.chemical_classificationresorcinareneFull PaperResorcinarenes010405 organic chemistryChemistryinclusion compoundsOrganic ChemistryGeneral ChemistryFull PapersResorcinareneX-ray diffraction0104 chemical sciencesCrystallographyIntramolecular forceProton NMRTwo-dimensional nuclear magnetic resonance spectroscopyröntgenkristallografiaChemistry – A European Journal
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Structural analysis of two foldamer-type oligoamides – the effect of hydrogen bonding on solvate formation, crystal structures and molecular conforma…

2012

Author's Final draft The crystal structures and molecular conformations of two foldamer-type oligoamides were analyzed. One polymorphic form and seven solvates were found for N¹,N³-bis(2-benzamidophenyl)benzene-1,3-dicarboxamide (the benzene variant), and two polymorphic forms and six solvates for N²,N⁶-bis(2-benzamidophenyl)pyridine-2,6-dicarboxamide (the pyridine variant). Three crystal structures of the benzene variant and seven structures of the pyridine variant were solved using single crystal X-ray diffraction. The crystal structures showed that the different modes of intramolecular hydrogen bonding strongly affect the conformation and folding of the molecules, which is most evidently…

kristallografiafoldameeriHydrogen bondStereochemistryFoldamerGeneral ChemistryCrystal structurekidetiedeCondensed Matter PhysicsoligoamideFolding (chemistry)chemistry.chemical_compoundCrystallographychemistryoligoamidifoldamerIntramolecular forcePyridineMoleculeGeneral Materials Scienceta116Single crystalCrystEngComm
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Alkyl-Substituted Aminobis(phosphonates) : Efficient Precipitating Agents for Rare Earth Elements, Thorium, and Uranium in Aqueous Solutions

2021

The efficient and environmentally sustainable separation process for rare earth elements (REE), especially for adjacent lanthanoids, remains a challenge due to the chemical similarity of REEs. Tetravalent actinoids, thorium, and traces of uranium are also present in concentrates of REEs, making their separation relevant. This study reports six simple water-soluble aminobis(phosphonate) ligands, RN[CH2P(O)(OH)2]2 (1 R = CH2CH3, 2 R = (CH2)2CH3, 3 R = (CH2)3CH3, 4 R = (CH2)4CH3, 5 R = (CH2)5CH3, 6 R = CH2CH(C2H5)(CH2)3CH3) as precipitating agents for REEs, Th, and U, as well as gives insight into the coordination modes of the utilized ligands with REEs at the molecular level. Aminobis(phospho…

titrationsaostusligandsmetalslanthanidestitrausliganditprecipitationmetallit
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Exploring the self-assembly of resorcinarenes : from molecular level interactions to mesoscopic structures

2012

UV-vis spectroscopyresorcinareneantibacterial silverionitspektroskopiaLangmuir-Blodgett filmsolid lipid nanoparticlemolekyylitfluorescence spectroscopysupramolecular chemistrystructural chemistryNMR spectroscopyorgaaninen kemiahost-guest chemistrytoiminnalliset materiaalitpinnoitteetX-ray crystallography
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Crystal Structures and Density Functional Theory Calculations of o-and p-Nitroaniline Derivatives: Combined Effect of Hydrogen Bonding and aromatic i…

2013

The interplay of strong and weak hydrogen bonds, dipole–dipole interactions, and aromatic interactions of o- and p-nitroaniline derivatives was studied by combining crystal structure analysis and density functional theory (DFT) calculations. Crystal structures of four 2-nitroaniline derivatives, 2-((2-nitrophenyl)amino)ethyl methanesulfonate (1A), 2-((2-nitrophenyl)amino)ethyl 4-methylbenzenesulfonate (2A), N,N′-((1,3-phenylenebis(oxy))bis(ethane-2,1-diyl))bis(2-nitroaniline) (3A), and N-(2-chloroethyl)-2-nitroaniline (4A), and crystal structures of three 4-nitroaniline derivatives, 2-((4-nitrophenyl)amino)ethyl methanesulfonate (1B), 2-((4-nitrophenyl)amino)ethyl 4-methylbenzenesulfonate (…

kristallografiaorganic complexesorgaaninen kemialaskennallinen kemiakidetiede
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Anion Responsive Molecular Switch Based on a Doubly‐Strapped Calix[4]pyrrole

2022

A calix[4]pyrrole receptor bearing two proximally meso - meso linking isophthaloyl straps displays open and closed states depending on the calix[4]pyrrole conformation. In the crystal structures and in non-polar solvent, the calix[4]pyrrole adopts open 1,3-alternate conformation with straps on the sides. Anion binding triggers a closed state of the receptor providing two types of interactions with an aromatic benzoate guest: hydrogen bonds from the pyrrolic groups and π ··· π interactions from the phenyl groups of the straps. Slow exchange dynamics was observed on the NMR timescale indicating that benzoate, acetate and chloride anions, which bind with relatively low affinity get kinetically…

kemialliset sidoksetNMR spectroscopyvetysidoksetanionitcalix[4]pyrrolessupramolekulaarinen kemiaNMR-spektroskopiaheterosykliset yhdisteetanionssupramolecular chemistrymolecular switch
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Controlling quaternary structure assembly: subunit interface engineering and crystal structure of dual chain avidin.

2006

Dual chain avidin (dcAvd) is an engineered avidin form, in which two circularly permuted chicken avidin monomers are fused into one polypeptide chain. DcAvd can theoretically form two different pseudotetrameric quaternary assemblies because of symmetry at the monomer-monomer interfaces. Here, our aim was to control the assembly of the quaternary structure of dcAvd. We introduced the mutation I117C into one of the circularly permuted domains of dcAvd and scanned residues along the 1-3 subunit interface of the other domain. Interestingly, V115H resulted in a single, disulfide locked quaternary assembly of dcAvd, whereas I117H could not guide the oligomerisation process even though it stabilis…

Models MolecularStereochemistryProtein subunitBiotinGene ExpressionCrystal structureCrystallography X-RayLigandsProtein EngineeringProtein–protein interactionchemistry.chemical_compoundBiotinStructural BiologyAnimalsDisulfidesProtein Structure QuaternaryMolecular BiologyChromatography High Pressure LiquidbiologyProtein engineeringHydrogen-Ion ConcentrationAvidinCrystallographyProtein SubunitsMonomerchemistryMutationbiology.proteinChromatography GelThermodynamicsProtein quaternary structureChickensAvidinJournal of molecular biology
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Alkyl-Substituted Aminobis(phosphonates)Efficient Precipitating Agents for Rare Earth Elements, Thorium, and Uranium in Aqueous Solutions

2021

The efficient and environmentally sustainable separation process for rare earth elements (REE), especially for adjacent lanthanoids, remains a challenge due to the chemical similarity of REEs. Tetravalent actinoids, thorium, and traces of uranium are also present in concentrates of REEs, making their separation relevant. This study reports six simple water-soluble aminobis(phosphonate) ligands, RN[CH2P(O)(OH)2]2 (1 R = CH2CH3, 2 R = (CH2)2CH3, 3 R = (CH2)3CH3, 4 R = (CH2)4CH3, 5 R = (CH2)5CH3, 6 R = CH2CH(C2H5)(CH2)3CH3) as precipitating agents for REEs, Th, and U, as well as gives insight into the coordination modes of the utilized ligands with REEs at the molecular level. Aminobis(phospho…

LanthanideAqueous solutionLigandGeneral Chemical EngineeringInorganic chemistrychemistry.chemical_element02 engineering and technologyGeneral Chemistry010402 general chemistry021001 nanoscience & nanotechnology01 natural sciencesPhosphonate0104 chemical sciencesSeparation processchemistry.chemical_compoundChemistryDeprotonationchemistryTitrationScandium0210 nano-technologyQD1-999ACS Omega
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Crystal Structures and Density Functional Theory Calculations of o-and p-Nitroaniline Derivatives: Combined Effect of Hydrogen Bonding and aromatic i…

2013

The interplay of strong and weak hydrogen bonds, dipole–dipole interactions, and aromatic interactions of o- and p-nitroaniline derivatives was studied by combining crystal structure analysis and density functional theory (DFT) calculations. Crystal structures of four 2-nitroaniline derivatives, 2-((2-nitrophenyl)amino)ethyl methanesulfonate (1A), 2-((2-nitrophenyl)amino)ethyl 4-methylbenzenesulfonate (2A), N,N′-((1,3-phenylenebis(oxy))bis(ethane-2,1-diyl))bis(2-nitroaniline) (3A), and N-(2-chloroethyl)-2-nitroaniline (4A), and crystal structures of three 4-nitroaniline derivatives, 2-((4-nitrophenyl)amino)ethyl methanesulfonate (1B), 2-((4-nitrophenyl)amino)ethyl 4-methylbenzenesulfonate (…

ta214Ethyl methanesulfonateta114Hydrogen bondIntermolecular forceAromaticityGeneral ChemistryCrystal structureCondensed Matter PhysicsRing (chemistry)Nitroanilinechemistry.chemical_compoundCrystallographychemistryComputational chemistryGeneral Materials ScienceDensity functional theoryta116Crystal Growth and Design
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Oligoamide Foldamers as Helical Chloride Receptors-the Influence of Electron-Withdrawing Substituents on Anion-Binding Interactions.

2019

The anion-binding properties of three closely related oligoamide foldamers were studied using NMR spectroscopy, isothermal titration calorimetry and mass spectrometry, as well as DFT calculations. The 1 H NMR spectra of the foldamers in [D6 ]acetone solution revealed partial preorganization by intramolecular hydrogen bonding, which creates a suitable cavity for anion binding. The limited size of the cavity, however, enabled efficient binding by the inner amide protons only for the chloride anion resulting in the formation of a thermodynamically stable 1:1 complex. All 1:1 chloride complexes displayed a significant favourable contribution of the entropy term. Most likely, this is due to the …

anionitreceptors010402 general chemistry01 natural sciencesBiochemistryChloridesupramolecular chemistryhost-guest systemschemistry.chemical_compoundAmidesupramolekulaarinen kemiamedicinefoldamersAnion bindingta116010405 organic chemistryChemistryHydrogen bondOrganic ChemistryFoldamerIsothermal titration calorimetryGeneral ChemistryNuclear magnetic resonance spectroscopy0104 chemical sciencesCrystallographyProton NMRanionsmedicine.drugChemistry, an Asian journal
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Resorcinarene bis-crown silver complexes and their application as antibacterial Langmuir-Blodgett films

2012

Silver complexes of a cation binding supramolecular host, resorcinarene bis-crown (CNBC5) with propyl, nonyl, decyl and undecyl alkyl chains were investigated by NMR titration, picrate extraction and single crystal X-ray diffraction. Binding studies showed that both 1 : 1 and 1 : 2 (host-Ag(+)) complexes are present in solution with only a slight effect of the lower rim alkyl chain length on the binding constants (log K 4.0-4.2 for 1 : 2 complexes). Solid state complexes of the resorcinarene bis-crowns bearing either C(3) or C(11) chains were obtained. Single crystal X-ray analyses showed that both derivatives bind silver ions by metal-arene and Ag···O coordination from the crown ether brid…

Cation bindingSilverPhenylalaninePicrateInorganic chemistrySupramolecular chemistryCrystallography X-RayBiochemistryLangmuir–Blodgett filmchemistry.chemical_compoundCoordination ComplexesPolymer chemistryAmphiphileEscherichia coliPhysical and Theoretical Chemistryta116Escherichia coli InfectionsAlkylCrown etherchemistry.chemical_classificationMolecular StructureOrganic ChemistryResorcinareneAnti-Bacterial AgentschemistryCalixarenesOrganic & Biomolecular Chemistry
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Cation binding resorcinarene bis-crowns: the effect of lower rim alkyl chain length on crystal packing and solid lipid nanoparticles

2012

A group of seven resorcinarene bis-crown ethers (CNBC5) with two polyether bridges at the upper rim and either propyl, butyl, pentyl, heptyl, nonyl, decyl or undecyl groups at the lower rim were synthesized and their binding properties with Cs+ were investigated by NMR titration. The bis-crowns form 1:2 complexes with Cs+ with binding constants of logK 4–5. Crystal structures of bis-crowns and their Cs+ and K+ complexes were studied and different packing motifs were found depending on the alkyl chain length. Short ethyl, propyl and butyl alkyl chains gave a layer or pillar packing where the polar and non-polar regions cannot be distinguished, whereas longer pentyl and decyl chains formed bi…

Cation bindingkaliumStereochemistryydinmagneettinen resonanssiCyclohexane conformationsolid lipid nanoparticleamphiphileCrystal structureCatalysisCrystalcesiumAmphiphilesupramolekyylikemiaMaterials Chemistrykiinteä lipidipartikkelisupramolekulaarinen kemiaMoleculemacrocyclic compoundta116Alkylkaliksareeniitsejärjestäytyminenchemistry.chemical_classificationresorcinareneChemistryGeneral Chemistrycaesiumself-assemblyResorcinarenekompleksiCrystallographynuclear magnetic resonanceamfifiilimakrosyklinen yhdistecalixarenecomplexröntgenkristallografiaresorsinareeni
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Supramolecular chirality and symmetry breaking of fluoride complexes of achiral foldamers

2017

Aromatic oligoamide foldamers containing a central pyridine-2,6-dicarbonyl motif are partially preorganized to favor the binding of fluoride anions. In the solid state, the foldamer-fluoride complexes form achiral, polar and chiral crystal structures depending on the chemical structure of the foldamer. One of the six foldamers studied here, a C2v symmetrical foldamer (1), formed repeatedly chiral crystal structures when crystallized with tetra-butylammonium fluoride, showing supramolecular bulk chirality and symmetry breaking in crystallization.

Supramolecular chiralitySupramolecular chemistrychiralityCrystal structure010402 general chemistrychemistry01 natural sciencessymmetry breakingsupramolecular chemistrylaw.inventionanion complexationchemistry.chemical_compoundlawGeneral Materials SciencemoleculesfoldamersSymmetry breakingCrystallizationcrystallographyta116symmetryfluorides010405 organic chemistryChemistryFoldamerGeneral ChemistryCondensed Matter Physics0104 chemical sciencesCrystallographyChirality (chemistry)FluorideanionsCrystEngComm
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Inverted molecular cups: 1-D and 2-D Ag(I) coordination polymers from resorcinarene bis-thiacrowns

2016

Resorcinarene bis-thiacrown hosts 1–3 were prepared and crystallized with silver trifluoroacetate yielding one and two dimensional Ag coordination polymers. The complexation of silver in exo-cavity fashion folds the thiacrown bridges inwards transforming the resorcinarene hosts into inverted molecular cups. The silver cations were coordinated to the resorcinarene ligands and trifluoroacetate anions, which act as monodentate or bidendate bridging ligands between the metal ions. Argentophilic Ag···Ag (2.93–3.38 Å) interactions supported by two bridging carboxylate anions were found in two of the structures, whereas longer Ag···Ag distances were observed if only one anion connected the silver …

coordination polymersresorcinarenesmacrocyclic ligands
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ChemInform Abstract: Self-Assembly of Amphiphilic Calixarenes and Resorcinarenes in Water

2011

The calixarenes and resorcinarenes are macrocyclic phenolic molecules that can be modified “a facon” and a wide range of chemical modification strategies have been published over the last 30 years. Because of their remarkable structural properties and their relative ease of chemical modification, they represent excellent and highly versatile bases to design complex building blocks capable of self-assembly and molecular recognition. They have been widely studied for their ability to form supramolecular structures targeting a wide range of applications. The possibility to regio(rim)-selectively modify these macrocycles with different polar and apolar moieties provides synthetic chemists with …

Molecular recognitionChemistryAmphiphileCalixareneSupramolecular chemistryChemical modificationMoleculeNanotechnologyGeneral MedicineSelf-assemblyChemInform
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Conformational polymorphism and amphiphilic properties of resorcinarene octapodands

2010

o-Nitroaniline functionalized resorcinarene octapodands 1-5 with pendant methyl, ethyl, pentyl, nonyl or 1-decenyl groups, respectively, were synthesized and their structural properties investigated using X-ray crystallography and NMR spectroscopy. The upper rim of each podand is identical containing flexible side arms, in which rotation around the -OCH(2)CH(2)N- linkers create excellent possibilities for polymorphism. Two conformational polymorphs of acetone solvate of 2 were identified containing different side arm orientation and crystal packing. Compound 1 crystallized from acetone and nitromethane yielding two pseudopolymorphs with different packing motifs. The longer alkyl chains of 3…

chemistry.chemical_classificationChemistryOrganic ChemistryNuclear magnetic resonance spectroscopyResorcinareneCrystal engineeringBiochemistryNitroanilinePolymorphism (materials science)AmphiphilePolymer chemistryMonolayerPhysical and Theoretical Chemistryta116AlkylOrganic & Biomolecular Chemistry
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Oligoamide Foldamers as Helical Chloride Receptors : the Influence of Electron-Withdrawing Substituents on Anion-Binding Interactions

2019

The anion‐binding properties of three closely related oligoamide foldamers were studied using NMR spectroscopy, isothermal titration calorimetry and mass spectrometry, as well as DFT calculations. The 1H NMR spectra of the foldamers in [D6]acetone solution revealed partial preorganization by intramolecular hydrogen bonding, which creates a suitable cavity for anion binding. The limited size of the cavity, however, enabled efficient binding by the inner amide protons only for the chloride anion resulting in the formation of a thermodynamically stable 1:1 complex. All 1:1 chloride complexes displayed a significant favourable contribution of the entropy term. Most likely, this is due to the re…

anionitsupramolekulaarinen kemiareceptorsfoldamershost-guest systems
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Self-assembly of amphiphilic calixarenes and resorcinarenes in water

2010

The calixarenes and resorcinarenes are macrocyclic phenolic molecules that can be modified “a facon” and a wide range of chemical modification strategies have been published over the last 30 years. Because of their remarkable structural properties and their relative ease of chemical modification, they represent excellent and highly versatile bases to design complex building blocks capable of self-assembly and molecular recognition. They have been widely studied for their ability to form supramolecular structures targeting a wide range of applications. The possibility to regio(rim)-selectively modify these macrocycles with different polar and apolar moieties provides synthetic chemists with …

Molecular recognitionChemistryAmphiphileCalixareneMaterials ChemistrySupramolecular chemistryChemical modificationMoleculeNanotechnologyGeneral ChemistrySelf-assemblyCatalysisNew Journal of Chemistry
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Solid lipid nanoparticles from amphiphilic calixpyrroles

2016

Abstract Hypothesis Macrocyclic amphiphiles form interesting self-assembling structures, including solid lipid nanoparticles, which have potential applications in drug encapsulation. Aryl-extended calixpyrroles, which act as anion binding hosts, are expected to form solid lipid nanoparticles, even though the alkyl chains have unusual perpendicular geometry with respect to the hydrophilic head group. The preparation conditions and the alkyl chain length should affect the size and stability of the particles. Experiments Solid lipid nanoparticles of two aryl-extended calixpyrroles with resorcinol walls and either meso-dodecyl or meso-methyl alkyl chains were compared. Ethanolic solutions of th…

Nanoparticleamphiphilesolid lipid nanoparticle02 engineering and technology010402 general chemistry01 natural sciencesBiomaterialszeta potentialColloid and Surface ChemistryDynamic light scatteringSolid lipid nanoparticleZeta potentialnanoparticle tracking analysisOrganic chemistrySurface chargeAnion bindingcalixpyrroleta116Alkylchemistry.chemical_classificationdynamic light scattering021001 nanoscience & nanotechnology540104 chemical sciencesSurfaces Coatings and FilmsElectronic Optical and Magnetic MaterialschemistryChemical engineeringParticle size0210 nano-technologymacrocycle
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Inverted molecular cups: 1-D and 2-D Ag(I) coordination polymers from resorcinarene bis-thiacrowns

2016

Resorcinarene bis-thiacrown hosts 1–3 were prepared and crystallized with silver trifluoroacetate yielding one and two dimensional Ag coordination polymers. The complexation of silver in exo-cavity fashion folds the thiacrown bridges inwards transforming the resorcinarene hosts into inverted molecular cups. The silver cations were coordinated to the resorcinarene ligands and trifluoroacetate anions, which act as monodentate or bidendate bridging ligands between the metal ions. Argentophilic Ag⋯Ag (2.93–3.38 A) interactions supported by two bridging carboxylate anions were found in two of the structures, whereas longer Ag⋯Ag distances were observed if only one anion connected the silver cati…

DenticityMetal ions in aqueous solutionInorganic chemistry010402 general chemistry01 natural sciencesMetalchemistry.chemical_compoundresorcinarenesGeneral Materials ScienceCarboxylateta116Alkylchemistry.chemical_classification010405 organic chemistryGeneral ChemistryPolymerResorcinareneCondensed Matter Physics0104 chemical sciencesSolventCrystallographycoordination polymerschemistryvisual_artvisual_art.visual_art_mediummacrocyclic ligandsCrystEngComm
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CCDC 1449685: Experimental Crystal Structure Determination

2016

Related Article: Kaisa Helttunen, Maija Nissinen|2016|CrystEngComm|18|4944|doi:10.1039/C6CE00243A

Space GroupCrystallographycatena-[(mu-281420-tetrapentyl-6121824-tetramethoxy-410:1622-bis(22'-(sulfanediylbis((ethane-21-diyl)sulfanediyl))di(ethoxy))calix[4]arene)-tetrakis(mu-trifluoroacetato)-(trifluoroacetato)-penta-silver ethanol solvate hydrate]Crystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1022891: Experimental Crystal Structure Determination

2015

Related Article: Aku Suhonen, Ian S. Morgan, Elisa Nauha, Kaisa Helttunen, Heikki M. Tuononen, Maija Nissinen|2015|Cryst.Growth Des.|15|2602|doi:10.1021/acs.cgd.5b00424

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersNN'-(13-Phenylenebis(sulfonylimino-21-phenylene))dibenzamide 12-dichloroethane solvateExperimental 3D Coordinates
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CCDC 1552171: Experimental Crystal Structure Determination

2017

Related Article: Kaisa Helttunen, Riia Annala, Aku Suhonen, Elisa Nauha, Juha Linnanto, Maija Nissinen|2017|CrystEngComm|19|5184|doi:10.1039/C7CE01109A

Space GroupCrystallographyCrystal SystemCrystal Structuretetrabutylammonium fluoride N2N6-bis{2-[(2-nitrobenzene-1-carbonyl)amino]phenyl}pyridine-26-dicarboxamideCell ParametersExperimental 3D Coordinates
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CCDC 1022892: Experimental Crystal Structure Determination

2015

Related Article: Aku Suhonen, Ian S. Morgan, Elisa Nauha, Kaisa Helttunen, Heikki M. Tuononen, Maija Nissinen|2015|Cryst.Growth Des.|15|2602|doi:10.1021/acs.cgd.5b00424

Space GroupCrystallographyCrystal SystemNN'-(13-Phenylenebis(sulfonylimino-21-phenylene))dibenzamide tetrahydrofuran solvateCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1042084: Experimental Crystal Structure Determination

2015

Related Article: Kaisa Helttunen, Tiia-Riikka Tero, Maija Nissinen|2015|CrystEngComm|17|3667|doi:10.1039/C5CE00311C

Space GroupCrystallographydi-cesium C-methyl tetramethoxy resorcinarene bis-crown-5 bis(hexafluorophosphate) acetone solvateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 930278: Experimental Crystal Structure Determination

2013

Related Article: Kaisa Helttunen, Lauri Lehtovaara, Hannu Häkkinen, and Maija Nissinen|2013|Cryst.Growth Des.|13|3603|doi:10.1021/cg4005714

Space GroupCrystallographyCrystal SystemCrystal Structure2-((4-Nitrophenyl)amino)ethyl methanesulfonateCell ParametersExperimental 3D Coordinates
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CCDC 1042079: Experimental Crystal Structure Determination

2015

Related Article: Kaisa Helttunen, Tiia-Riikka Tero, Maija Nissinen|2015|CrystEngComm|17|3667|doi:10.1039/C5CE00311C

Space GroupCrystallographyCrystal SystemCrystal Structure6243048-tetramethoxy-2265154-tetramethyl-9121518213336394245-decaoxaheptacyclo[27.19.3.3525.038.02253.02732.04650]tetrapentaconta-1(48)3572224272931464952-dodecaeneCell ParametersExperimental 3D Coordinates
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CCDC 1963708: Experimental Crystal Structure Determination

2020

Related Article: Małgorzata Pamuła, Maija Nissinen, Kaisa Helttunen|2020|Chem.-Eur.J.|26|7374|doi:10.1002/chem.201905211

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters281420-tetraethyl-4101622-tetramethoxy-6121824-tetrakis(2-(p-toluenesulfonato)ethoxy)calix[4]areneExperimental 3D Coordinates
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CCDC 930279: Experimental Crystal Structure Determination

2013

Related Article: Kaisa Helttunen, Lauri Lehtovaara, Hannu Häkkinen, and Maija Nissinen|2013|Cryst.Growth Des.|13|3603|doi:10.1021/cg4005714

2-((2-Nitrophenyl)amino)ethyl 4-methylbenzenesulfonateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1552172: Experimental Crystal Structure Determination

2017

Related Article: Kaisa Helttunen, Riia Annala, Aku Suhonen, Elisa Nauha, Juha Linnanto, Maija Nissinen|2017|CrystEngComm|19|5184|doi:10.1039/C7CE01109A

Space GroupCrystallographytetrabutylammonium fluoride N2-(2-aminophenyl)-N6-{2-[(benzenecarbonyl)amino]phenyl}pyridine-26-dicarboxamideCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1552170: Experimental Crystal Structure Determination

2017

Related Article: Kaisa Helttunen, Riia Annala, Aku Suhonen, Elisa Nauha, Juha Linnanto, Maija Nissinen|2017|CrystEngComm|19|5184|doi:10.1039/C7CE01109A

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameterstetrabutylammonium fluoride N2-{2-[(benzenecarbonyl)amino]phenyl}-N6-{2-[(4-cyanobenzene-1-carbonyl)amino]phenyl}pyridine-26-dicarboxamide hydrateExperimental 3D Coordinates
researchProduct

CCDC 973532: Experimental Crystal Structure Determination

2014

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25262728-tetrakis(Dodecyloxy)pentacyclo[19.3.1.137.1913.11519]octacosa-1(25)3(28)469(27)101215(26)16182123-dodecaene-5111723-tetracarboxylic acid pyridine solvateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1552175: Experimental Crystal Structure Determination

2017

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Space GroupCrystallographyN2N6-bis{2-[(2-nitrobenzene-1-carbonyl)amino]phenyl}pyridine-26-dicarboxamideCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1042086: Experimental Crystal Structure Determination

2015

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Space GroupCrystallographyCrystal SystemCrystal StructureCell Parametersaqua-(6243048-tetramethoxy-2265154-tetramethyl-9121518213336394245-decaoxaheptacyclo[27.19.3.3525.038.02253.02732.04650]tetrapentaconta-1(48)3572224272931464952-dodecaene)-silver(i) trifluoromethanesulfonate ethanol solvate sesquihydrateExperimental 3D Coordinates
researchProduct

CCDC 2175936: Experimental Crystal Structure Determination

2022

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Space GroupCrystallographyCrystal SystemCrystal Structure44'4''4'''-(5101520-tetramethyl-51015202224-hexahydroporphyrin-5101520-tetrayl)tetraphenol hexanedinitrile ethanol solvate monohydrateCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1022889: Experimental Crystal Structure Determination

2015

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Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersNN'-(13-Phenylenebis(sulfonylimino-21-phenylene))dibenzamide unknown solvateExperimental 3D Coordinates
researchProduct

CCDC 2175934: Experimental Crystal Structure Determination

2022

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Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameterspyridinium chloride bis(44'4''4'''-(5101520-tetramethyl-51015202224-hexahydroporphyrin-5101520-tetrayl)tetraphenol) acetonitrile solvateExperimental 3D Coordinates
researchProduct

CCDC 1042087: Experimental Crystal Structure Determination

2015

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2202632-tetramethoxy-24303639-tetramethyl-58111417-pentaoxahexacyclo[19.15.3.12529.13135.0438.01823]hentetraconta-1318202225(41)262831(40)323437-dodecaene-2834-diol chloroform monohydrateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1022890: Experimental Crystal Structure Determination

2015

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Space GroupCrystallographyCrystal SystemCrystal StructureNN'-(13-Phenylenebis(sulfonylimino-21-phenylene))dibenzamide acetonitrile solvateCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 930281: Experimental Crystal Structure Determination

2013

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Space GroupCrystallographyCrystal SystemCrystal StructureNN'-(13-Phenylenebis(oxyethane-21-diyl))bis(2-nitroaniline)Cell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1042083: Experimental Crystal Structure Determination

2015

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Space GroupCrystallographyCrystal System6243048-tetramethoxy-2265154-tetramethyl-9121518213336394245-decaoxaheptacyclo[27.19.3.3525.038.02253.02732.04650]tetrapentaconta-1(48)3572224272931464952-dodecaene chloroform solvateCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1552173: Experimental Crystal Structure Determination

2017

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Space GroupCrystallographytetra-n-butylammonium N2-(2-benzamidophenyl)-N6-phenylpyridine-26-dicarboxamide fluorideCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1552174: Experimental Crystal Structure Determination

2017

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Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersN-(2-aminophenyl)-2-nitrobenzamideExperimental 3D Coordinates
researchProduct

CCDC 1042088: Experimental Crystal Structure Determination

2015

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2202632-tetramethoxy-24303639-tetramethyl-58111417-pentaoxahexacyclo[19.15.3.12529.13135.0438.01823]hentetraconta-1318202225(41)262831(40)323437-dodecaene-2834-diol acetonitrile solvateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1042082: Experimental Crystal Structure Determination

2015

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Space GroupCrystallographyCrystal SystemCrystal StructureC-methyl tetramethoxy resorcinarene bis-crown-5 dichloromethane methanol solvateCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 930282: Experimental Crystal Structure Determination

2013

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Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D CoordinatesN-(2-Chloroethyl)-2-nitroaniline
researchProduct

CCDC 1449684: Experimental Crystal Structure Determination

2016

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Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinatescatena-[(mu-281420-tetraethyl-6121824-tetramethoxy-410:1622-bis(22'-(sulfanediylbis((ethane-21-diyl)sulfanediyl))di(ethoxy))calix[4]arene)-tris(trifluoroacetato)-(ethanol)-tri-silver ethanol solvate hemihydrate]
researchProduct

CCDC 1449686: Experimental Crystal Structure Determination

2016

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catena-[bis(mu-281420-tetrapentyl-6121824-tetramethoxy-410:1622-bis(22'-(propane-13-diyldisulfanediyl)di(ethoxy))calix[4]arene)-tetrakis(mu-trifluoroacetato)-(trifluoroacetato)-penta-silver ethanol solvate monohydrate]Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1449683: Experimental Crystal Structure Determination

2016

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Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameterscatena-[bis(mu-281420-tetraethyl-6121824-tetramethoxy-410:1622-bis(22'-(sulfanediylbis((ethane-21-diyl)sulfanediyl))di(ethoxy))calix[4]arene)-tetrakis(trifluoroacetato)-tetra-silver dichloromethane ethanol unknown solvate tetrahydrate]Experimental 3D Coordinates
researchProduct

CCDC 1042081: Experimental Crystal Structure Determination

2015

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Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters6243048-tetramethoxy-2265154-tetramethyl-9121518213336394245-decaoxaheptacyclo[27.19.3.3525.038.02253.02732.04650]tetrapentaconta-1(48)3572224272931464952-dodecaene acetonitrile solvateExperimental 3D Coordinates
researchProduct

CCDC 1552169: Experimental Crystal Structure Determination

2017

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Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinatestetrabutylammonium fluoride N2N6-bis{2-[(benzenecarbonyl)amino]phenyl}pyridine-26-dicarboxamide
researchProduct

CCDC 1552176: Experimental Crystal Structure Determination

2017

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Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameterstetra-n-butylammonium fluoride N1N3-bis{2-[(benzenecarbonyl)amino]phenyl}benzene-13-dicarboxamideExperimental 3D Coordinates
researchProduct

CCDC 930280: Experimental Crystal Structure Determination

2013

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Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates2-((4-Nitrophenyl)amino)ethyl 4-methylbenzenesulfonate
researchProduct

CCDC 1042080: Experimental Crystal Structure Determination

2015

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Space GroupCrystallographyCrystal SystemCrystal Structure6243048-tetramethoxy-2265154-tetramethyl-9121518213336394245-decaoxaheptacyclo[27.19.3.3525.038.02253.02732.04650]tetrapentaconta-1(48)3572224272931464952-dodecaeneCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 2175935: Experimental Crystal Structure Determination

2022

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Space GroupCrystallographyCrystal System1H-imidazol-3-ium chloride bis(44'4''4'''-(5101520-tetramethyl-51015202224-hexahydroporphyrin-5101520-tetrayl)tetraphenol) acetonitrile solvateCrystal StructureCell ParametersExperimental 3D Coordinates
researchProduct

CCDC 1042085: Experimental Crystal Structure Determination

2015

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Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters(mu-630-dimethoxy-2265154-tetramethyl-24-(methoxy)-48-(methoxy)-9121518213336394245-decaoxaheptacyclo[27.19.3.3525.038.02253.02732.04650]tetrapentaconta-1(48)3572224272931464952-dodecaene)-di-silver hexafluorophosphate hydrofluoride acetone solvate hydrateExperimental 3D Coordinates
researchProduct

CCDC 930283: Experimental Crystal Structure Determination

2013

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Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameterst-Butyl 2-((4-nitrophenyl)amino)ethyl carbonateExperimental 3D Coordinates
researchProduct

CCDC 930277: Experimental Crystal Structure Determination

2013

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Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters2-((2-Nitrophenyl)amino)ethyl methanesulfonateExperimental 3D Coordinates
researchProduct

CCDC 1963709: Experimental Crystal Structure Determination

2020

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Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters281420-tetraethyl-4101622-tetramethoxy-6121824-tetrakis(2-(p-tolylmethoxy)ethoxy)calix[4]areneExperimental 3D Coordinates
researchProduct

CCDC 1524058: Experimental Crystal Structure Determination

2017

UDAKUI : 6,12,18,24-tetramethoxy-2,8,14,20-tetrapropyl-4,10,16,22-tetrahydroxycalix[4]arene acetone solvate Space Group: P21/n, Cell: a 11.7707(4)Å b 17.4447(6)Å c 21.7775(7)Å, α 90.00° β 105.261(2)° γ 90.00° Work published 2017 via Cambridge Crystallographic Data Centre.

calixarenemacrocyclesupramolecular chemistry
researchProduct

CCDC 1523875: Experimental Crystal Structure Determination

2017

UDARID : ethyl N-benzoylalaninate Space Group: P212121, Cell: a 5.2938(2)Å b 12.1920(8)Å c 17.7130(4)Å, α 90° β 90° γ 90° Work published 2017 via Cambridge Crystallographic Data Centre.

esterificationalanineamino acid
researchProduct

CCDC 1524101: Experimental Crystal Structure Determination

2017

UCUZOK : 6,12,18,24-tetramethoxy-2,8,14,20-tetranonyl-4,10,16,22-tetrahydroxycalix[4]arene propan-2-ol solvate Space Group: P-1, Cell: a 12.27090(10)Å b 13.96500(10)Å c 19.53620(10)Å, α 83.2880(1)° β 89.0250(1)° γ 84.9650(1)° Work published 2017 via Cambridge Crystallographic Data Centre.

resorcinarenesolvatecalixarenemacrocyclesupramolecular chemistry
researchProduct

CCDC 1524052: Experimental Crystal Structure Determination

2017

UDAKOC : diaqua-(μ-1,13-dioxa-4,7,10,16,19,22-hexaazacyclotetracosane)-bis(perchlorato)-di-copper(ii) diperchlorate tetrahydrate Space Group: P21/c, Cell: a 11.8763(3)Å b 13.9146(4)Å c 13.4024(4)Å, α 90.00° β 123.439(2)° γ 90.00° Work published 2017 via Cambridge Crystallographic Data Centre.

azacrownmacrocycleazacorandsupramolecular chemistrycopper complex
researchProduct