Lewis Base Catalyzed Intramolecular Reduction of Salicylaldehydes by Pinacol-Derived Chlorohydrosilane

2,2′:6′,2″-Terpyridine Trimethylplatinum(IV) Iodide Complexes as Bifunctional Halogen Bond Acceptors

Three new organometallic trimethylplatinum(IV) iodide complexes of 2,2′:6′,2″-terpyridines have been synthesized and characterized by 1H NMR spectroscopy, mass spectrometry, elemental analysis, and single crystal X-ray diffraction analysis. The X-ray crystal structures of PtMe3I(L) complexes 1–3 {L for 1 = 4′-chloro-2,2′:6′,2″-terpyridine, 2 = 4′-(4-cyanophenyl)-2,2′:6′,2″-terpyridine, and 3 = 4′-(4-tolyl)-2,2′:6′,2″-terpyridine} reveal distorted octahedral coordination geometry of the platinum(IV) metal centers with bidentate coordination of the terpyridine ligands. Complexation of 1–3 with iodopentafluorobenzene (IPFB) afforded single-crystal structures of halogen bond (XB) complexes 1a–3…

Stimuli-responsive bile acid-based metallogels forming in aqueous media

Abstract The synthesis and gelation properties of a picolinic acid conjugated bile acid derivative in the presence of metal salts along with the stimuli-responsiveness of the systems are reported. The gels are formed in the presence of Cu 2+ ions in the solvent systems composed of 30–50% of organic solvent (MeOH, acetonitrile, or acetone) in water. The gels respond to various stimuli: they can be formed upon sonication or shaking, and their gel–sol transformation can be triggered by a variety of chemical species. NMR, MS, and SEM techniques are exploited in order to gain a deeper insight on the self-assembled systems.

Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution

A novel eight-membered macrocycle of the hemicucurbit[n]uril family, chiral (all-R)-cyclohexanohemicucurbit[8]uril (cycHC[8]) binds anions in a purely protic solvent with remarkable selectivity. The cycHC[8] portals open and close to fully encapsulate anions in a 1 : 1 ratio, resembling a molecular Pac-Man™. Comprehensive gas, solution and solid phase studies prove that the binding is governed by the size, shape and charge distribution of the bound anion. Gas phase studies show an order of SbF6− ≈ PF6− > ReO4− > ClO4− > SCN− > BF4− > HSO4− > CF3SO3− for anion complexation strength. An extensive crystallographic study reveals the preferred orientations of the anions within the octahedral cav…

Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor

A simple 18-crown-6-based bis-urea receptor R(1) was synthesized in three steps from a commercial starting material. The receptor's behavior toward anions, cations, and ion pairs was studied in solution with (1)H NMR, in solid state with single-crystal X-ray diffraction, and in gas phase with mass spectrometry. In 4:1 CDCl3/dimethyl sulfoxide solution the receptor's binding preference of halide anions is I(-) < Br(-) < Cl(-) following the trend of the hydrogen-bonding acceptor ability of the anions. The receptor shows a remarkable positive cooperativity toward halide anions Cl(-), Br(-), and I(-) when complexed with Na(+), K(+), or Rb(+). The solid-state binding modes of R(1) with alkali an…

The Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides

Three water-soluble N-alkyl ammonium resorcinarene chlorides decorated with terminal hydroxyl groups at the lower rims were synthesized and characterized. The receptors were decorated at the upper rim with either terminal hydroxyl, rigid cyclohexyl, or flexible benzyl groups. The binding affinities of these receptors toward three viologen derivatives, two of which possess an acetylmethyl group attached to one of the pyridine nitrogens, in water were investigated via 1H NMR spectroscopy, fluorescence spectroscopy, and isothermal titration calorimetry (ITC). ITC quantification of the binding process gave association constants of up to 103 M-1. Analyses reveal a spontaneous binding process whi…

Tetrameric and Dimeric [N∙∙∙I+∙∙∙N] Halogen-Bonded Supramolecular Cages

Tripodal N-donor ligands are used to form halogen-bonded assemblies via structurally analogous Ag+-complexes. Selective formation of discrete tetrameric I6L4 and dimeric I3L2 halonium cages, wherein multiple [N∙∙∙I+∙∙∙N] halogen bonds are used in concert, can be achieved by using sterically rigidified cationic tris(1-methyl-1-azonia-4-azabicyclo[2.2.2]octane)-mesitylene ligand, L1(PF6)3, and flexible ligand 1,3,5-tris(imidazole-1-ylmethyl)-2,4,6-trimethylbenzene, L2, respectively. The iodonium cages, I6L14(PF6)18 and I3L22(PF6)3, were obtained through the [N∙∙∙Ag+∙∙∙N] → [N∙∙∙I+∙∙∙N] cation exchange reaction between the corresponding Ag6L14(PF6)18 and Ag3L22(PF6)3 coordination cages, prepar…

Simultaneous Endo- and Exo-Complex Formation of Pyridine[4]arene Dimer with Neutral and Anionic Guests

The formation of complexes between hexafluorophosphate (PF6−) and tetraisobutyloctahydroxypyridine[4]arene has been thoroughly studied in the gas phase (ESI‐QTOF‐MS, IM‐MS, DFT calculations), in the solid state (X‐ray crystallography), and in chloroform solution (1H, 19F, and DOSY NMR spectroscopy). In all states of matter, simultaneous endo complexation of solvent molecules and exo complexation of a PF6− anion within a pyridine[4]arene dimer was observed. While similar ternary complexes are often observed in the solid state, this is a unique example of such behavior in the gas phase. peerReviewed

The inherent structural instability: concentration-dependent transformation of pyrogallarene to pyrogallarene lactones.

Pyrogallarene shows concentration-dependent instability in dilute solutions resulting in elimination of two ketene molecules and formation of pyrogallarene lactones. This unexpected phenomenon, which is not observed with resorcinarenes, highlights the significance of the four hydroxyl groups at 2-position for the molecular characteristics of pyrogallarenes.

Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers

Pyridine[4]arenes have previously been considered as anion binding hosts due to the electron-poor nature of the pyridine ring. Herein, we demonstrate the encapsulation of Me4N+ cations inside a dimeric hydrogen-bonded pyridine[4]arene capsule, which contradicts with earlier assumptions. The complexation of a cationic guest inside the pyridine[4]arene dimer has been detected and studied by multiple gas-phase techniques, ESI-QTOF-MS, IRMPD, and DT-IMMS experiments, as well as DFT calculations. The comparison of classical resorcinarenes with pyridinearenes by MS and NMR experiments reveals clear differences in their host–guest chemistry and implies that cation encapsulation in pyridine[4]arene…

Ion mobility mass spectrometry – an efficient tool for the analysis of conformational switch of macrocyclic receptors upon anion binding

Interactions between anions and synthetic macrocyclic receptors belong to the extensively explored area of research due to the particularly important functions of anions in biological and environmental sciences. Structures of anion-macrocycle complexes are closely related to their function, highlighting the importance of structural analysis of the complexes. Here, we discuss the application of ion mobility mass spectrometry (IM-MS) and theoretical calculations to the structural analysis of tetralactam macrocycles (M) with varying flexibility and structural properties, and their complexes with anions [M + X]−. Collision cross section (CCS) values obtained from both direct drift tube (DT) and…

Role of C–H···Au and Aurophilic Supramolecular Interactions in Gold–Thione Complexes

The role of noncovalent gold–hydrogen and aurophilic interactions in the formation of extended molecular systems of gold complexes was studied. Three new gold compounds with a heterocyclic thione ligand N-methylbenzothiazole-2-thione (mbtt), namely, [AuCl(mbtt)] (1), [AuBr(mbtt)] (2), and [Au(mbtt)2][AuI2]1–n[I3]n (3), were synthesized and characterized. The halide ligand had a considerable effect on the complex structures and thus to noncovalent contacts. Intermolecular C–H···Au and aurophilic Au···Au contacts were the dominant noncovalent interactions in structures 1–3 determining the supramolecular arrays of the gold complexes. In 1 and 2, unusual intermolecular C–H···Au gold–hydrogen co…

Nondestructive Size Determination of Thiol-Stabilized Gold Nanoclusters in Solution by Diffusion Ordered NMR Spectroscopy

Diffusion ordered NMR spectroscopy (DOSY) was used as an analytical tool to estimate the size of thiol-stabilized gold nanoclusters in solution, namely, phenylethanethiol (PET) stabilized Au25(PET)18, Au38(PET)24, and Au144(PET)60. This was achieved by determining the diffusion coefficient and hydrodynamic radius from solution samples that were confirmed to be monodispersed by electrospray ionization mass spectrometry. The average cluster diameters obtained by this technique were estimated to be 1.7, 2.2, and 3.1 nm for the Au25(PET)18, Au38(PET)24, and Au144(PET)60 nanoclusters, respectively, which were shown to agree well with the average diameters of the corresponding single crystal or t…

Noncovalent Saccharide Recognition by Means of a Tetrakis(bile acid)-Porphyrin Conjugate: Selectivity, Cooperation, and Stability

Molecular recognition of Glu, Glc 2 -Glc 6 and Mal 3 by a tetrakis(bile acid)―porphyrin conjugate has been studied by using ESI-FTICR mass spectrometry. The bile acid conjugate was observed to form 1:1 noncovalent complexes with saccharides. The conjugate was found to have size-selectivity towards saccharides with three or more glucose residues. The Glc 3 and Glc 4 also formed kinetically the most stable complexes. The electron capture dissociation (ECD) experiments revealed that in complexation of an oligosaccharide three glucose residues interact with the bile acid conjugate, whereas additional glucose residues are susceptible to fragmentation. The ECD results also showed the significance…

Ion mobility-mass spectrometry of supramolecular complexes and assemblies

Despite their structural and functional differences, synthetic supramolecular assemblies share many similarities with biological assemblies, especially enzymes. The assemblies can be on the same length scale, and their structures and guest binding are typically governed by non-covalent interactions. Thus, only relatively weak interactions define the shape of a synthetic supramolecule or the secondary and tertiary structure of a protein, such that the resulting dynamism makes structure elucidation challenging. For biomolecules such as peptides, proteins, glycans and lipids this has often been tackled using ion mobility–mass spectrometry (IM-MS), whereby analyte ions are separated according t…

Construction of Coordination Polymers from Semirigid Ditopic 2,2′-Biimidazole Derivatives: Synthesis, Crystal Structures, and Characterization

Eight coordination polymers (CPs), {[Ag(L1)]ClO4}n (1), {[Ag(L2)1.5]ClO4·C2H3N}n (2a), {[Ag(L2)]ClO4}n (2b), [Zn(L1)Cl2]n (3), {[Zn(L2)Cl2]·CHCl3}n (4), {[Cu(L1)2Cl]Cl·H2O}n (5), [Cu2(L2)(μ-Cl)2]n (6), and [Cu4(L2)(μ-Cl)4]n (7) were synthesized via self-assembly of corresponding metal ions and biimidazole based ditopic ligands, 1,1′-bis(pyridin-3-ylmethyl)-2,2′-biimidazole L1 and 1,1′-bis(pyridin-4-ylmethyl)-2,2′-biimidazole L2. These ligands possess conformational flexibility and two pairs of coordination sites: pyridine nitrogen (NPy) atoms and imidazole nitrogen (NIm) atoms. Depending on the metal center in CPs, the biimidazole compounds act as tetra- (1, 7), tri- (2a), or bidentate (2a,…

Size- and Structure-Selective Noncovalent Recognition of Saccharides by Tetraethyl and Tetraphenyl Resorcinarenes in the Gas Phase

The noncovalent complexation of tetraethyl and tetraphenyl resorcinarenes with mono-, di-, and oligosaccharides was studied with negative-polarization electrospray ionization quadrupole ion trap and electrospray ionization Fourier-transform ion cyclotron resonance mass-spectrometric analysis. The saccharides formed 1:1 complexes with deprotonated resorcinarenes, which exhibited clear size and structure selectivity in their complexation. In the case of the monosaccharides, hexoses formed much more abundant and kinetically stable complexes than pentoses or deoxyhexoses. A comparison of the mono-, di-, and oligosaccharides revealed that both the relative abundance and stability of the complexe…

Selective gas adsorption by calixarene-based porous octahedral M32 coordination cages

Giant octahedral M32 coordination cages were prepared via self-assembly of sulfonylcalix[4]arene-supported tetranuclear M(II) clusters (M = Co, Ni) with hybrid linker based on tris(dipyrrinato)cobalt(III) complexes appended with peripherical carboxylic groups. Due to intrinsic and extrinsic porosity, the obtained solid-state supramolecular architectures demonstrated good performance as adsorbents for the separation of industrially important gases mixtures. peerReviewed

Superchiral Pd 3 L 6 Coordination Complex and Its Reversible Structural Conversion into Pd 3 L 3 Cl 6 Metallocycles

Large, non-symmetrical, inherently chiral bispyridyl ligand L derived from natural ursodeoxycholic bile acid was used for square-planar coordination of tetravalent Pd(II) , yielding the cationic single enantiomer of superchiral coordination complex 1 Pd3 L6 containing 60 well-defined chiral centers in its flower-like structure. Complex 1 can readily be transformed by addition of chloride into a smaller enantiomerically pure cyclic trimer 2 Pd3 L3 Cl6 containing 30 chiral centers. This transformation is reversible and can be restored by the addition of silver cations. Furthermore, a mixture of two constitutional isomers of trimer, 2 and 2', and dimer, 3 and 3', can be obtained directly from …

Metallophilic interactions in polymeric group 11 thiols

Three polymeric group 11 transition metal polymers featuring metallophilic interactions were obtained directly via self-assembly of metal ions and 4-pyridinethiol ligands. In the cationic [Cu2(S-pyH)4]n2+ with [ZnCl4]n2− counterion (1) and in the neutral [Ag(S-py) (S-pyH)]n (2) 4-pyridinethiol (S-pyH) and its deprotonated form (S-py) are coordinated through the sulfur atom. Both ligands are acting as bridging ligands linking the metal centers together. In the solid state, the gold(I) polymer [Au(S-pyH)2]Cl (3) consists of the repeating cationic [Au(S-pyH)2]+ units held together by aurophilic interactions. Compound 1 is a zig-zag chain, whereas the metal chains in the structures of 2 and 3 a…

Simultane endo - und exo -Komplexbildung von Pyridin[4]aren-Dimeren mit neutralen und anionischen Gästen

Ion-Pair Complexation with Dibenzo[21]Crown-7 and Dibenzo[24]Crown-8 bis-Urea Receptors

Synthesis and ion-pair complexation properties of novel ditopic bis-urea receptors based on dibenzo[21]crown-7 (R(1) ) and dibenzo[24]crown-8 (R(2) ) scaffolds have been studied in the solid state, solution, and gas phase. In a 4:1 CDCl3 /[D6 ]DMSO solution, both receptors clearly show positive heterotropic cooperativity toward halide anions when complexed with Rb(+) or Cs(+) , with the halide affinity increasing in order I(-) <Br(-) <Cl(-) . In solution, the rubidium complexes of both receptors have higher halide affinities compared to the caesium complexes. However, Rb(+) and Cs(+) complexes of R(2) show stronger affinities toward all the studied anions compared to the corresponding catio…

Macrocyclic complexes based on [N⋯I⋯N]+ halogen bonds

New 1–2 nm macrocyclic iodine(I) complexes prepared VIA a simple ligand exchange reaction manifest rigid 0.5–1 nm cavities that bind the hexafluorophosphate anion in the gas phase. The size of the cavities and the electrostatic interactions with the iodine(I) cations influence the anion binding properties of these macrocyclic complexes.

Charge-Assisted Halogen Bonding in an Ionic Cavity of a Coordination Cage Based on a Copper(I) Iodide Cluster.

The design of molecular containers capable of selective binding of specific guest molecules presents an interesting synthetic challenge in supramolecular chemistry. Here, we report the synthesis and structure of a coordination cage assembled from Cu3I4– clusters and tripodal cationic N-donor ligands. Owing to the localized permanent charges in the ligand core the cage binds iodide anions in specific regions within the cage by ionic interactions. This allows the selective binding of bromomethanes as secondary guest species within cage promoted by halogen bonding, which was confirmed by single crystal X-ray diffraction. peerReviewed

The geometry of the silver 1,1′-dibenzyl-2,2′-biimidazole complexes

Abstract The argentophilic interactions and interactions of weakly coordinated nitrate and water with silver metal were studied by investigating the reaction of 1,1′-dibenzyl-2,2′-biimidazole (Bn2bim) with silver nitrate. Three new silver complexes [Ag4(Bn2bim)4(NO3)2]·4(CH3CH2OH)·2(NO3)·0.5(H2O) (1), [Ag4(Bn2bim)4(H2O)4]·4(NO3) (2) and [Ag4(Bn2bim)4(NO3)4]·6(CH2Cl2)·2(H2O) (3) were synthesized and characterized. Complexes 1-3 have rare tetranuclear twisted closed cyclic structure with four bridging biimidazoles and variable nitrate/water ratio. The interactions between the nitrate ligand and Ag as well as water ligands and Ag are considered to be weak due to the ease of exchanging them. Th…

Halogen bonds with coordinative nature: halogen bonding in a S–I+–S iodonium complex†

A detailed study of unexpectedly strong iodonium–sulfur halogen bonds in [I(2-imidazolidinethione)2]+ is presented. The interactions are characterized by single-crystal X-ray diffraction, charge density analysis based on QTAIM calculations, mass spectrometry, and NMR spectroscopy. The results, small RIS = 0.7 and high interaction energy of −60 kJ mol−1, support a coordinative nature of the halogen bond between the iodonium ion and the sp2 hybridized sulfur atoms.

Oligoamide Foldamers as Helical Chloride Receptors-the Influence of Electron-Withdrawing Substituents on Anion-Binding Interactions.

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 …

Synthesis and characterization of Zwitterionic Zn(II) and Cu(II) coordination compounds with ring-substituted 2,2′-biimidazole derivatives

Zwitterionic coordination compounds with strongly asymmetrical charge distribution were synthesized and characterized. Ring-substituted biimidazoles were used as the primary ligands for Zn and Cu compounds. Formation of Zwitterionic coordination compound was found to be strongly dependent on the pH of the reaction medium as well as on the ring and nitrogen substituents of the ligand. Reaction of the Df-R2biim (Df-R2biim = 2,2′-bi-1R-imidazole-5,5′-dicarboxaldehyde, R = Me, Et or Pr) with ZnCl2 in neutral conditions led to binuclear compounds [Zn2Cl4(Df-R2biim)2] with two bridging ligands (1a–c). Reaction with CuCl2·2H2O gave neutral mononuclear compound [CuCl2(Df-Me2biim)] (1d) with chelati…

Hexagonal Microparticles from Hierarchical Self-Organization of Chiral Trigonal Pd3L6 Macrotetracycles

Construction of structurally complex architectures using inherently chiral, asymmetric, or multi-heterotopic ligands is a major challenge in metallosupramolecular chemistry. Moreover, the hierarchical self-organization of such complexes is unique. Here, we introduce a water-soluble, facially amphiphilic, amphoteric, chiral, asymmetric, and hetero-tritopic ligand derived from natural bile acid, ursodeoxycholic acid. We show that via the supramolecular transmetalation reaction, using nitrates of Cu(II) or Fe(III), and subsequently Pd(II), a superchiral Pd3L6 complex can be obtained. Even though several possible constitutional isomers of Pd3L6 could be formed, because of the ligand asymmetry a…

Synthesis, structure and photophysical properties of a highly luminescent terpyridine-diphenylacetylene hybrid fluorophore and its metal complexes

A new fluorescent terpyridyl-diphenylacetylene hybrid fluorophore 4′-[4-{(4-methoxyphenyl)ethynyl}phenyl]-2,2′:6′,2′′-terpyridine, L, was synthesized via Sonogashira cross-coupling of 4′-(4-bromophenyl)-2,2′:6′,2′′-terpyridine and 4-ethynylanisole in the presence of Pd(PPh3)4/CuI as a catalyst. The solid state structure of L shows a trans arrangement of pyridine nitrogen atoms along the interannular bond in the terpyridine domain. Five transition metal complexes of L, {[FeL2](CF3SO3)2 (1), [ZnL2](ClO4)2 (2), [CdL2](ClO4)2 (3), [RuL2](PF6)2 (4), and PtMe3IL (5)}, have also been synthesized and characterized by spectroscopic methods and single crystal X-ray analysis. The X-ray crystal structu…

Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution

A novel eight-membered macrocycle of the hemicucurbit[n]uril family, chiral (all-R)-cyclohexanohemicucurbit[8]uril (cycHC[8]) binds anions in a purely protic solvent with remarkable selectivity. The cycHC[8] portals open and close to fully encapsulate anions in a 1 : 1 ratio, resembling a molecular Pac-Man™. Comprehensive gas, solution and solid phase studies prove that the binding is governed by the size, shape and charge distribution of the bound anion. Gas phase studies show an order of SbF6− ≈ PF6− > ReO4− > ClO4− > SCN− > BF4− > HSO4− > CF3SO3− for anion complexation strength. An extensive crystallographic study reveals the preferred orientations of the anions within the octahedral cav…

Chemistry inside molecular containers in the gas phase.

Inner-phase chemical reactions of guest molecules encapsulated in a macromolecular cavity give fundamental insight into the relative stabilization of transition states by the surrounding walls of the host, thereby modelling the situation of substrates in enzymatic binding pockets. Although in solution several examples of inner-phase reactions are known, the use of cucurbiturils as macrocyclic hosts and bicyclic azoalkanes as guests has now enabled a systematic mass spectrometric investigation of inner-phase reactions in the gas phase, where typically the supply of thermal energy results in dissociation of the supramolecular host-guest assembly. The results reveal a sensitive interplay in wh…

Thermodynamically driven self-assembly of pyridinearene to hexameric capsules

Pyridinearene macrocycles have previously shown unique host–guest properties in their capsular dimers including endo complexation of neutral molecules and exo complexation of anions. Here, we demonstrate for the first time the formation of hydrogen bonded hexamer of tetraisobutyl-octahydroxypyridinearene in all three states of matter – gas phase, solution and solid-state. Cationic tris(bipyridine)ruthenium(II) template was found to stabilize the hexamer in gas phase, whereas solvent molecules do this in condensed phases. In solution, the capsular hexamer was found to be the thermodynamically favoured self-assembly product and transition from dimer to hexamer occurred in course of time. The …

Self-healing, luminescent metallogelation driven by synergistic metallophilic and fluorine–fluorine interactions

Square planar platinum(ii) complexes are attractive building blocks for multifunctional soft materials due to their unique optoelectronic properties. However, for soft materials derived from synthetically simple discrete metal complexes, achieving a combination of optical properties, thermoresponsiveness and excellent mechanical properties is a major challenge. Here, we report the rapid self-recovery of luminescent metallogels derived from platinum(ii) complexes of perfluoroalkyl and alkyl derivatives of terpyridine ligands. Using single crystal X-ray diffraction studies, we show that the presence of synergistic platinum-platinum (PtMIDLINE HORIZONTAL ELLIPSISPt) metallopolymerization and f…

Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides

Three water-soluble N-alkyl ammonium resorcinarene chlorides decorated with terminal hydroxyl groups at the lower rims were synthesized and characterized. The receptors were decorated at the upper rim with either terminal hydroxyl, rigid cyclohexyl, or flexible benzyl groups. The binding affinities of these receptors toward three viologen derivatives, two of which possess an acetylmethyl group attached to one of the pyridine nitrogens, in water were investigated via 1H NMR spectroscopy, fluorescence spectroscopy, and isothermal titration calorimetry (ITC). ITC quantification of the binding process gave association constants of up to 103 M–1. Analyses reveal a spontaneous binding process whi…

Towards low-energy-light-driven bistable photoswitches : ortho-fluoroaminoazobenzenes

AbstractThermally stable photoswitches that are driven with low-energy light are rare, yet crucial for extending the applicability of photoresponsive molecules and materials towards, e.g., living systems. Combined ortho-fluorination and -amination couples high visible light absorptivity of o-aminoazobenzenes with the extraordinary bistability of o-fluoroazobenzenes. Herein, we report a library of easily accessible o-aminofluoroazobenzenes and establish structure–property relationships regarding spectral qualities, visible light isomerization efficiency and thermal stability of the cis-isomer with respect to the degree of o-substitution and choice of amino substituent. We rationalize the exp…

Oligoamide Foldamers as Helical Chloride Receptors : the Influence of Electron-Withdrawing Substituents on Anion-Binding Interactions

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…

Selective encapsulation of a chloride anion in a 1H-pyrazole Cu2+ metallocage

A self-assembled metallobox from copper(ii) and two macrocycles containing 1H-pyrazole ligands has been prepared. The internal cavity of the box is able to selectively encapsulate a single chloride anion over any other halide anion.

Large Azobenzene Macrocycles : Formation and Detection by NMR and MS Methods

Azobenzene macrocycles are widely investigated as potential drug delivery systems and as part of molecular machines due to their photo-responsive properties. Herein, we detect the formation of a series of new azobenzene macrocycles that feature up to eight switchable repeating units. High-resolution mass spectrometry and ion mobility (IM) mass spectrometry experiments and 1H and diffusion-ordered spectroscopy (DOSY) NMR are used to detect the presence of the macrocycles that contain 10 to 40 aromatic rings in the gas phase and solution, respectively. The responsiveness of the Z-to-E photo-switching of the smallest of the macrocycles, exhibiting two azobenzene units and in total 10 aromatic …

Macrocyclic complexes based on [N⋯I⋯N]+ halogen bonds

New 1–2 nm macrocyclic iodine(I) complexes prepared VIA a simple ligand exchange reaction manifest rigid 0.5–1 nm cavities that bind the hexafluorophosphate anion in the gas phase. The size of the cavities and the electrostatic interactions with the iodine(I) cations influence the anion binding properties of these macrocyclic complexes. peerReviewed

Synthesis, structure and photophysical properties of a highly luminescent terpyridine-diphenylacetylene hybrid fluorophore and its metal complexes

A new fluorescent terpyridyl-diphenylacetylene hybrid fluorophore 4'-[4-{(4-methoxyphenyl)ethynyl}phenyl]-2,2':6',2''-terpyridine, L, was synthesized via Sonogashira cross-coupling of 4'-(4-bromophenyl)-2,2':6',2''-terpyridine and 4-ethynylanisole in the presence of Pd(PPh3)4/CuI as a catalyst. The solid state structure of L shows a trans arrangement of pyridine nitrogen atoms along the interannular bond in the terpyridine domain. Five transition metal complexes of L, {[FeL2](CF3SO3)2 (1), [ZnL2](ClO4)2 (2), [CdL2](ClO4)2 (3), [RuL2](PF6)2 (4), and PtMe3IL (5)}, have also been synthesized and characterized by spectroscopic methods and single crystal X-ray analysis. The X-ray crystal structu…

2-Methylresorcinarene: a very high packing coefficient in a mono-anion based dimeric capsule and the X-ray crystal structure of the tetra-anion

Mono- and tetra-deprotonated 2-methylresorcinarene anions (1 and 2) as their trans-1,4-diammoniumcyclohexane (TDAC)2+ inclusion complexes are reported. The mono-anion forms a fully closed dimeric capsule [1·H2O·MeOH]22− with a cavity volume of 165 Å3 and (TDAC)2+ as the guest with an extremely high packing coefficient, PC = 84.2%, while the tetra-anion forms a close-packed structure with two structurally isomeric tetra-anions 2a and 2b with a 50 : 50 ratio in the crystal lattice. peerReviewed

Noncovalent axial I∙∙∙Pt∙∙∙I interactions in platinum(II) complexes strengthen in the excited state

Abstract Coordination compounds of platinum(II) participate in various noncovalent axial interactions involving metal center. Weakly bound axial ligands can be electrophilic or nucleophilic; however, interactions with nucleophiles are compromised by electron density clashing. Consequently, simultaneous axial interaction of platinum(II) with two nucleophilic ligands is almost unprecedented. Herein, we report structural and computational study of a platinum(II) complex possessing such intramolecular noncovalent I⋅⋅⋅Pt⋅⋅⋅I interactions. Structural analysis indicates that the two iodine atoms approach the platinum(II) center in a “side‐on” fashion and act as nucleophilic ligands. According to c…

Spontaneous Resolution of an Electron‐Deficient Tetrahedral Fe4L4cage

A highly electron-deficient C3-symmetric tris(bipyridyl) ligand was prepared in four steps and used for the coordination of Fe(OTf)2, thereby resulting in the homochiral assembly of a new family of robust tetrahedral M4L4 cages. This homochiral T-symmetric cage containing a relatively large cavity of 330 A(3) is capable of encapsulating an anionic guest, as was determined by mass spectrometry, (19)F NMR spectroscopy, and finally shown from its crystal structure. Moreover, crystallization of the cage from CH3CN led to crystals containing both (ΔΔΔΔ and ΛΛΛΛ) enantiomers, while crystallization from CH3 OH resulted in crystals containing only the right-handed (ΔΔΔΔ) cage. The difference in the…

Chromophore-Protein Interplay During the Phytochrome Photocycle Revealed by Step-Scan FTIR Spectroscopy

Phytochrome proteins regulate many photoresponses of plants and microorganisms. Light absorption causes isomerization of the biliverdin chromophore, which triggers a series of structural changes to activate the signaling domains of the protein. However, the structural changes are elusive, and therefore the molecular mechanism of signal transduction remains poorly understood. Here, we apply two-color step-scan infrared spectroscopy to the bacteriophytochrome from Deinococcus radiodurans. We show by recordings in H2O and D2O that the hydrogen bonds to the biliverdin D-ring carbonyl become disordered in the first intermediate (Lumi-R) forming a dynamic microenvironment, then completely detach …

The complex formation of tetracyclohexylammonium C1-resorcinarene with various guests - an electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry study.

The complex formation of a tetraammonium C1-resorcinarene (R+4HCl) was studied using electrospray ionization Fourier transform ion cyclotron resonance (ESI-FTICR) mass spectrometry. Although R+4HCl easily loses its counter ions in the ESI process, a neutral self-assembled structure with an intramolecular circular hydrogen-bonded 16-membered -N(+)-H ... X(-) ... H-N(+)- array with ammonium ion as the charge-giving species was observed in the gas phase. In addition to chloride, several other counter ions were also studied. The size and basicity of the counter ion as well as the size of the charge-giving cation strongly affected the gas-phase stability of the self-assembled system. H/D exchang…

DOSY NMR, X-ray Structural and Ion-Mobility Mass Spectrometric Studies on Electron-Deficient and Electron-Rich M6L4 Coordination Cages.

A novel modular approach to electron-deficient and electron-rich M6L4 cages is presented. From the same starting compound, via a minor modulation of the synthesis route, two C3-symmetric ligands L1 and L2 with different electronic properties are obtained in good yield. The trifluoro-triethynylbenzene-based ligand L1 is more electron-deficient than the well-known 2,4,6-tri(4-pyridyl)-1,3,5-triazine, while the trimethoxy-triethynylbenzene-based ligand L2 is more electron-rich than the corresponding benzene analogue. Complexation of the ligands with cis-protected square-planar [(dppp)Pt(OTf)2] or [(dppp)Pd(OTf)2] corner-complexes yields two electron-deficient (1a and 1b) and two electron-rich …

Modulating the reaction pathway of phenyl diazonium ions using host–guest complexation with cucurbit[7]uril

Aryl diazonium ions are known to be an important intermediate in the divergent synthesis of azo compounds and substituted aromatics. The presence of more than one electrophilic center in a diazonium ion could lead to undesirable side reactions during a synthesis. Herein, we report that the electrophilic α-carbon on a phenyl diazonium [PhN2]+ ion can be selectively deactivated upon host–guest complexation with cucurbit[7]uril (CB7) in aqueous media, achieving a ∼60-fold increase in the half-life of [PhN2]+. Notably, however, the electrophilic nitrogen of the encapsulated diazonium ion remains active towards diazo coupling with strong nucleophiles, allowing the formation of azo compounds usin…

Solution- and gas-phase study of binding of ammonium and bisammonium hydrocarbons to oxacalix[4]arene carboxylate

Oxacalixarenes represent a distinctive class of macrocyclic compounds, which are closely related to the parent calixarene family, offering binding motifs characteristic of calixarenes and crown ethers. Nevertheless, they still lack extensive characterization in terms of molecular recognition properties and the subsequent practical applicability. We present here the results of binding studies of an oxacalix[4]arene carboxylate macrocycle toward a variety of organic ammonium cationic species. Our results show that the substituents attached to the guest ammonium compound largely influence the binding strengths of the host. Furthermore, we show that the characteristic binding pattern changes up…

Subcomponent Self-Assembly A Quick Way to New Metallogels

Subcomponent self-assembly, introduced by the Nitschke group,[1] is a process which allow complex structures to be generated from simple building blocks (generally aldehydes and amines). In this bottom-up approach, the building blocks spontaneously self-assemble around templates (usually metal ions) leading to a simultaneous covalent (C=N) and dative (N– metal) bonds formation. The method has been successfully used to construct well-defined metal-organic macrocycles, helicates, catenanes, rotaxanes, grids,[2] and cages.[3] Our field of interest lies not in building-up of defined structures but in designing gelator molecules for a formation of supramolecular gels as functional nanomaterials.…

Mononuclear Ru(II) PolyPyridyl Water Oxidation Catalysts Decorated with Perfluoroalkyl C 8 H 17 ‐Tag Bearing Chains

Experimental Confirmation of a Topological Isomer of the Ubiquitous Au25(SR)18 Cluster in the Gas Phase

High-resolution electrospray ionization ion mobility mass spectrometry has revealed a gas-phase isomer of the ubiquitous, extremely well-studied Au25(SR)18 cluster both in anionic and cationic form. The relative abundance of the isomeric structures can be controlled by in-source activation. The measured collision cross section of the new isomer agrees extremely well with a recent theoretical prediction (Matus, M. F.; et al. Chem. Commun. 2020, 56, 8087) corresponding to a Au25(SR)18– isomer that is energetically close and topologically connected to the known ground-state structure via a simple rotation of the gold core without breaking any Au–S bonds. The results imply that the structural d…

Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution† †Electronic supplementary information (ESI) available: MS, NMR, dynamic NMR and computational details and a DFT-based video of complexation. CCDC 1514736–1514741, 1521388. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc05058a Click here for additional data file. Click here for additional data file. Click here for additional data file.

Chiral (all-R)-cyclohexanohemicucurbit[8]uril binds anions in a 1 : 1 ratio in pure methanol like a molecular Pac-Man™ with remarkable selectivity based on the size, shape and charge distribution of the anion.

Tetrameric and Dimeric [N∙∙∙I+∙∙∙N] Halogen-Bonded Supramolecular Cages

Tripodal N‐donor ligands are used to form halogen‐bonded assemblies via structurally analogous Ag+‐complexes. Selective formation of discrete tetrameric I6L4 and dimeric I3L2 halonium cages, wherein multiple [N⋅⋅⋅I+⋅⋅⋅N] halogen bonds are used in concert, can be achieved by using sterically rigidified cationic tris(1‐methyl‐1‐azonia‐4‐azabicyclo[2.2.2]octane)‐mesitylene ligand, L1(PF6)3, and flexible ligand 1,3,5‐tris(imidazole‐1‐ylmethyl)‐2,4,6‐trimethylbenzene, L2, respectively. The iodonium cages, I6L14(PF6)18 and I3L22(PF6)3, were obtained through the [N⋅⋅⋅Ag+⋅⋅⋅N]→ [N⋅⋅⋅I+⋅⋅⋅N] cation exchange reaction between the corresponding Ag6L14(PF6)18 and Ag3L22(PF6)3 coordination cages, prepare…

Pd2Au36(SR)(24) cluster: structure studies

The location of the Pd atoms in Pd2Au36(SC2H4Ph)(24), is studied both experimentally and theoretically. X-ray photoelectron spectroscopy (XPS) indicates oxidized Pd atoms. Palladium K-edge extended X-ray absorption fine-structure (EXAFS) data clearly show Pd-S bonds, which is supported by far infrared spectroscopy and by comparing theoretical EXAFS spectra in R space and circular dichroism spectra of the staple, surface and core doped structures with experimental spectra.

Simultaneous endo and exo  Complex Formation of Pyridine[4]arene Dimers with Neutral and Anionic Guests

The formation of complexes between hexafluorophosphate (PF6- ) and tetraisobutyloctahydroxypyridine[4]arene has been thoroughly studied in the gas phase (ESI-QTOF-MS, IM-MS, DFT calculations), in the solid state (X-ray crystallography), and in chloroform solution (1 H, 19 F, and DOSY NMR spectroscopy). In all states of matter, simultaneous endo complexation of solvent molecules and exo complexation of a PF6- anion within a pyridine[4]arene dimer was observed. While similar ternary complexes are often observed in the solid state, this is a unique example of such behavior in the gas phase.

Triggering a transient organo-gelation system in a chemically active solvent

A transient organo-gelation system with spatiotemporal dynamic properties is described. Here, the solvent actively controls a complex set of equilibria that underpin the dynamic assembly event. The observed metastability is due to the in situ formation of a secondary solvent, acting as an antagonist against the primary solvent of the organogel. peerReviewed

Thermal expansion and magnetic properties of benzoquinone-bridged dinuclear rare-earth complexes.

The synthesis and structural characterization of two benzoquinone-bridged dinuclear rare-earth complexes [BQ(MCl2·THF3)2] (BQ = 2,5-bisoxide-1,4-benzoquinone; M = Y (1), Dy (2)) are described. Of these reported metal complexes, the dysprosium analogue 2 is the first discrete bridged dinuclear lanthanide complex in which both metal centres reside in pentagonal bipyramidal environments. Interestingly, both complexes undergo significant thermal expansion upon heating from 120 K to 293 K as illustrated by single-crystal X-ray and powder diffraction experiments. AC magnetic susceptibility measurements reveal that 2 does not show the slow relation of magnetization in zero dc field. The absent of …

CCDC 1406016: Experimental Crystal Structure Determination

Related Article: Kalle Kolari, Joona Sahamies, Elina Kalenius, Alexander S. Novikov, Vadim Yu Kukushkin, Matti Haukka|2016|Solid State Sciences|60|92|doi:10.1016/j.solidstatesciences.2016.08.005

CCDC 1478712: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Anniina Kiesilä, Elina Kalenius and Kari Rissanen|2016|Chem.-Eur.J.|22|14264|doi:10.1002/chem.201602362

CCDC 1473236: Experimental Crystal Structure Determination

Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Elina Kalenius, Robin H. A. Rasb and Kari Rissanen|2016|Chem.Commun.|52|8115|doi:10.1039/C6CC03289C

CCDC 1404481: Experimental Crystal Structure Determination

Related Article: Biswa Nath Ghosh, Manu Lahtinen, Elina Kalenius, Prasenjit Mal, Kari Rissanen|2016|Cryst.Growth Des.|16|2527|doi:10.1021/acs.cgd.5b01552

CCDC 1408386: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Elina Kalenius, and Kari Rissanen|2015|Inorg.Chem.|54|9154|doi:10.1021/acs.inorgchem.5b01577

CCDC 1062272: Experimental Crystal Structure Determination

Related Article: Pia Bonakdarzadeh, Filip Topić, Elina Kalenius, Sandip Bhowmik, Sota Sato, Michael Groessl, Richard Knochenmuss, Kari Rissanen|2015|Inorg.Chem.|54|6055|doi:10.1021/acs.inorgchem.5b01082

CCDC 1543476: Experimental Crystal Structure Determination

Related Article: Anniina Kiesilä, Lauri Kivijärvi, Ngong Kodiah Beyeh, Jani O. Moilanen, Michael Groessl, Tatiana Rothe, Sven Götz, Filip Topić, Kari Rissanen, Arne Lützen and Elina Kalenius|2017|Angew.Chem.,Int.Ed.|56|10942|doi:10.1002/anie.201704054

CCDC 1478717: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Anniina Kiesilä, Elina Kalenius and Kari Rissanen|2016|Chem.-Eur.J.|22|14264|doi:10.1002/chem.201602362

CCDC 1478716: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Anniina Kiesilä, Elina Kalenius and Kari Rissanen|2016|Chem.-Eur.J.|22|14264|doi:10.1002/chem.201602362

CCDC 1404479: Experimental Crystal Structure Determination

Related Article: Biswa Nath Ghosh, Manu Lahtinen, Elina Kalenius, Prasenjit Mal, Kari Rissanen|2016|Cryst.Growth Des.|16|2527|doi:10.1021/acs.cgd.5b01552

CCDC 1953708: Experimental Crystal Structure Determination

Related Article: Ondřej Jurček, Nonappa, Elina Kalenius, Pia Jurček, Juha M. Linnanto, Rakesh Puttreddy, Hennie Valkenier, Nikolay Houbenov, Michal Babiak, Miroslav Peterek, Anthony P. Davis, Radek Marek, Kari Rissanen|2021|Cell Reports Physical Science|2|100303|doi:10.1016/j.xcrp.2020.100303

CCDC 1525503: Experimental Crystal Structure Determination

Related Article: Ngong Kodiah Beyeh, Hyun Hwa Jo, Igor Kolesnichenko, Fangfang Pan, Elina Kalenius, Eric V. Anslyn, Robin H. A. Ras, Kari Rissanen|2017|J.Org.Chem.|82|5198|doi:10.1021/acs.joc.7b00449

CCDC 1408378: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Elina Kalenius, and Kari Rissanen|2015|Inorg.Chem.|54|9154|doi:10.1021/acs.inorgchem.5b01577

CCDC 1408380: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Elina Kalenius, and Kari Rissanen|2015|Inorg.Chem.|54|9154|doi:10.1021/acs.inorgchem.5b01577

CCDC 1554863: Experimental Crystal Structure Determination

Related Article: Lotta Turunen, Anssi Peuronen, Samu Forsblom, Elina Kalenius, Manu Lahtinen and Kari Rissanen|2017|Chem.-Eur.J.|23|11714|doi:10.1002/chem.201702655

CCDC 1408383: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Elina Kalenius, and Kari Rissanen|2015|Inorg.Chem.|54|9154|doi:10.1021/acs.inorgchem.5b01577

CCDC 1478713: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Anniina Kiesilä, Elina Kalenius and Kari Rissanen|2016|Chem.-Eur.J.|22|14264|doi:10.1002/chem.201602362

CCDC 1554861: Experimental Crystal Structure Determination

Related Article: Lotta Turunen, Anssi Peuronen, Samu Forsblom, Elina Kalenius, Manu Lahtinen and Kari Rissanen|2017|Chem.-Eur.J.|23|11714|doi:10.1002/chem.201702655

CCDC 1478715: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Anniina Kiesilä, Elina Kalenius and Kari Rissanen|2016|Chem.-Eur.J.|22|14264|doi:10.1002/chem.201602362

CCDC 1407136: Experimental Crystal Structure Determination

Related Article: Pia Bonakdarzadeh, Fangfang Pan, Elina Kalenius, Ondřej Jurček, Kari Rissanen|2015|Angew.Chem.,Int.Ed.|54|14890|doi:10.1002/anie.201507295

CCDC 1514740: Experimental Crystal Structure Determination

Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A

CCDC 1443455: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Elina Kalenius, Matti Haukka|2016|Inorg.Chim.Acta|453|298|doi:10.1016/j.ica.2016.08.015

CCDC 1443459: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Elina Kalenius, Matti Haukka|2016|Inorg.Chim.Acta|453|298|doi:10.1016/j.ica.2016.08.015

CCDC 1545350: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Evgeny Bulatov, Elina Kalenius, Matti Haukka|2017|Cryst.Growth Des.|17|5918|doi:10.1021/acs.cgd.7b01034

CCDC 1545346: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Evgeny Bulatov, Elina Kalenius, Matti Haukka|2017|Cryst.Growth Des.|17|5918|doi:10.1021/acs.cgd.7b01034

CCDC 1949029: Experimental Crystal Structure Determination

Related Article: Kalle Kolari, Evgeny Bulatov, Rajendhraprasad Tatikonda, Kia Bertula, Elina Kalenius, Nonappa, Matti Haukka|2020|Soft Matter|16|2795|doi:10.1039/C9SM02186H

CCDC 1478709: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Anniina Kiesilä, Elina Kalenius and Kari Rissanen|2016|Chem.-Eur.J.|22|14264|doi:10.1002/chem.201602362

CCDC 1443458: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Elina Kalenius, Matti Haukka|2016|Inorg.Chim.Acta|453|298|doi:10.1016/j.ica.2016.08.015

CCDC 1478711: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Anniina Kiesilä, Elina Kalenius and Kari Rissanen|2016|Chem.-Eur.J.|22|14264|doi:10.1002/chem.201602362

CCDC 1408384: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Elina Kalenius, and Kari Rissanen|2015|Inorg.Chem.|54|9154|doi:10.1021/acs.inorgchem.5b01577

CCDC 1408381: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Elina Kalenius, and Kari Rissanen|2015|Inorg.Chem.|54|9154|doi:10.1021/acs.inorgchem.5b01577

CCDC 1514737: Experimental Crystal Structure Determination

Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A

CCDC 1008273: Experimental Crystal Structure Determination

Related Article: Biswa Nath Ghosh, Filip Topić, Prasit Kumar Sahoo, Prasenjit Mal, Jarno Linnera, Elina Kalenius, Heikki M. Tuononen, Kari Rissanen|2015|Dalton Trans.|44|254|doi:10.1039/C4DT02728K

CCDC 2211278: Experimental Crystal Structure Determination

Related Article: Anssi Peuronen, Anni Taponen, Elina Kalenius, Ari Lehtonen, Manu Lahtinen|2023|Angew.Chem.,Int.Ed.|62|e202215689|doi:10.1002/anie.202215689

CCDC 1406018: Experimental Crystal Structure Determination

Related Article: Kalle Kolari, Joona Sahamies, Elina Kalenius, Alexander S. Novikov, Vadim Yu Kukushkin, Matti Haukka|2016|Solid State Sciences|60|92|doi:10.1016/j.solidstatesciences.2016.08.005

CCDC 1545345: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Evgeny Bulatov, Elina Kalenius, Matti Haukka|2017|Cryst.Growth Des.|17|5918|doi:10.1021/acs.cgd.7b01034

CCDC 2211279: Experimental Crystal Structure Determination

Related Article: Anssi Peuronen, Anni Taponen, Elina Kalenius, Ari Lehtonen, Manu Lahtinen|2023|Angew.Chem.,Int.Ed.|62|e202215689|doi:10.1002/anie.202215689

CCDC 941619: Experimental Crystal Structure Determination

Related Article: Biswa Nath Ghosh, Filip Topić, Prasit Kumar Sahoo, Prasenjit Mal, Jarno Linnera, Elina Kalenius, Heikki M. Tuononen, Kari Rissanen|2015|Dalton Trans.|44|254|doi:10.1039/C4DT02728K

CCDC 1408379: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Elina Kalenius, and Kari Rissanen|2015|Inorg.Chem.|54|9154|doi:10.1021/acs.inorgchem.5b01577

CCDC 1473237: Experimental Crystal Structure Determination

Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Elina Kalenius, Robin H. A. Rasb and Kari Rissanen|2016|Chem.Commun.|52|8115|doi:10.1039/C6CC03289C

CCDC 1907903: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Massimo Cametti, Elina Kalenius, Antonino Famulari, Kari Rissanen, Matti Haukka|2019|Eur.J.Inorg.Chem.|2019|4463|doi:10.1002/ejic.201900579

CCDC 1404485: Experimental Crystal Structure Determination

Related Article: Biswa Nath Ghosh, Manu Lahtinen, Elina Kalenius, Prasenjit Mal, Kari Rissanen|2016|Cryst.Growth Des.|16|2527|doi:10.1021/acs.cgd.5b01552

CCDC 1949030: Experimental Crystal Structure Determination

Related Article: Kalle Kolari, Evgeny Bulatov, Rajendhraprasad Tatikonda, Kia Bertula, Elina Kalenius, Nonappa, Matti Haukka|2020|Soft Matter|16|2795|doi:10.1039/C9SM02186H

CCDC 1406017: Experimental Crystal Structure Determination

Related Article: Kalle Kolari, Joona Sahamies, Elina Kalenius, Alexander S. Novikov, Vadim Yu Kukushkin, Matti Haukka|2016|Solid State Sciences|60|92|doi:10.1016/j.solidstatesciences.2016.08.005

CCDC 1525501: Experimental Crystal Structure Determination

Related Article: Ngong Kodiah Beyeh, Hyun Hwa Jo, Igor Kolesnichenko, Fangfang Pan, Elina Kalenius, Eric V. Anslyn, Robin H. A. Ras, Kari Rissanen|2017|J.Org.Chem.|82|5198|doi:10.1021/acs.joc.7b00449

CCDC 1408388: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Elina Kalenius, and Kari Rissanen|2015|Inorg.Chem.|54|9154|doi:10.1021/acs.inorgchem.5b01577

CCDC 1541300: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Evgeny Bulatov, Elina Kalenius, Matti Haukka|2017|Cryst.Growth Des.|17|5918|doi:10.1021/acs.cgd.7b01034

CCDC 1404484: Experimental Crystal Structure Determination

Related Article: Biswa Nath Ghosh, Manu Lahtinen, Elina Kalenius, Prasenjit Mal, Kari Rissanen|2016|Cryst.Growth Des.|16|2527|doi:10.1021/acs.cgd.5b01552

CCDC 1994847: Experimental Crystal Structure Determination

Related Article: Javier Pitarch-Jarque, Hermas R. Jiménez, Elina Kalenius, Salvador Blasco, Alberto Lopera, M. Paz Clares, Kari Rissanen, Enrique García-España|2021|Dalton Trans.|50|9010|doi:10.1039/D1DT01302E

CCDC 1493777: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Massimo Cametti, Elina Kalenius, Antonino Famulari, Kari Rissanen, Matti Haukka|2019|Eur.J.Inorg.Chem.|2019|4463|doi:10.1002/ejic.201900579

CCDC 1062271: Experimental Crystal Structure Determination

Related Article: Pia Bonakdarzadeh, Filip Topić, Elina Kalenius, Sandip Bhowmik, Sota Sato, Michael Groessl, Richard Knochenmuss, Kari Rissanen|2015|Inorg.Chem.|54|6055|doi:10.1021/acs.inorgchem.5b01082

CCDC 1008276: Experimental Crystal Structure Determination

Related Article: Biswa Nath Ghosh, Filip Topić, Prasit Kumar Sahoo, Prasenjit Mal, Jarno Linnera, Elina Kalenius, Heikki M. Tuononen, Kari Rissanen|2015|Dalton Trans.|44|254|doi:10.1039/C4DT02728K

CCDC 1408376: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Elina Kalenius, and Kari Rissanen|2015|Inorg.Chem.|54|9154|doi:10.1021/acs.inorgchem.5b01577

CCDC 1554864: Experimental Crystal Structure Determination

Related Article: Lotta Turunen, Anssi Peuronen, Samu Forsblom, Elina Kalenius, Manu Lahtinen and Kari Rissanen|2017|Chem.-Eur.J.|23|11714|doi:10.1002/chem.201702655

CCDC 1443464: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Elina Kalenius, Matti Haukka|2016|Inorg.Chim.Acta|453|298|doi:10.1016/j.ica.2016.08.015

CCDC 1493776: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Massimo Cametti, Elina Kalenius, Antonino Famulari, Kari Rissanen, Matti Haukka|2019|Eur.J.Inorg.Chem.|2019|4463|doi:10.1002/ejic.201900579

CCDC 2211276: Experimental Crystal Structure Determination

Related Article: Anssi Peuronen, Anni Taponen, Elina Kalenius, Ari Lehtonen, Manu Lahtinen|2023|Angew.Chem.,Int.Ed.|62|e202215689|doi:10.1002/anie.202215689

CCDC 1443457: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Elina Kalenius, Matti Haukka|2016|Inorg.Chim.Acta|453|298|doi:10.1016/j.ica.2016.08.015

CCDC 1408387: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Elina Kalenius, and Kari Rissanen|2015|Inorg.Chem.|54|9154|doi:10.1021/acs.inorgchem.5b01577

CCDC 1443461: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Elina Kalenius, Matti Haukka|2016|Inorg.Chim.Acta|453|298|doi:10.1016/j.ica.2016.08.015

CCDC 1408382: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Elina Kalenius, and Kari Rissanen|2015|Inorg.Chem.|54|9154|doi:10.1021/acs.inorgchem.5b01577

CCDC 1478714: Experimental Crystal Structure Determination

Related Article: Toni Mäkelä, Anniina Kiesilä, Elina Kalenius and Kari Rissanen|2016|Chem.-Eur.J.|22|14264|doi:10.1002/chem.201602362

CCDC 1407137: Experimental Crystal Structure Determination

Related Article: Pia Bonakdarzadeh, Fangfang Pan, Elina Kalenius, Ondřej Jurček, Kari Rissanen|2015|Angew.Chem.,Int.Ed.|54|14890|doi:10.1002/anie.201507295

CCDC 1514738: Experimental Crystal Structure Determination

Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A

CCDC 1514739: Experimental Crystal Structure Determination

Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A

CCDC 1443456: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Elina Kalenius, Matti Haukka|2016|Inorg.Chim.Acta|453|298|doi:10.1016/j.ica.2016.08.015

CCDC 1994844: Experimental Crystal Structure Determination

Related Article: Javier Pitarch-Jarque, Hermas R. Jiménez, Elina Kalenius, Salvador Blasco, Alberto Lopera, M. Paz Clares, Kari Rissanen, Enrique García-España|2021|Dalton Trans.|50|9010|doi:10.1039/D1DT01302E

CCDC 1404482: Experimental Crystal Structure Determination

Related Article: Biswa Nath Ghosh, Manu Lahtinen, Elina Kalenius, Prasenjit Mal, Kari Rissanen|2016|Cryst.Growth Des.|16|2527|doi:10.1021/acs.cgd.5b01552

CCDC 1545348: Experimental Crystal Structure Determination

Related Article: Rajendhraprasad Tatikonda, Evgeny Bulatov, Elina Kalenius, Matti Haukka|2017|Cryst.Growth Des.|17|5918|doi:10.1021/acs.cgd.7b01034

CCDC 1062270: Experimental Crystal Structure Determination

Related Article: Pia Bonakdarzadeh, Filip Topić, Elina Kalenius, Sandip Bhowmik, Sota Sato, Michael Groessl, Richard Knochenmuss, Kari Rissanen|2015|Inorg.Chem.|54|6055|doi:10.1021/acs.inorgchem.5b01082

Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution

Chiral (all-R)-cyclohexanohemicucurbit[8]uril binds anions in a 1 : 1 ratio in pure methanol like a molecular Pac-Man™ with remarkable selectivity based on the size, shape and charge distribution of the anion.

CCDC 1493778: Experimental Crystal Structure Determination

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CCDC 1408377: Experimental Crystal Structure Determination

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CCDC 1408385: Experimental Crystal Structure Determination

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CCDC 1478710: Experimental Crystal Structure Determination

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