Tetraiodoethynyl resorcinarene cavitands as multivalent halogen bond donors

The first examples of iodoethynyl resorcinarene cavitands as rigid 3D halogen bond (XB) donor molecules are presented. These concave macrocycles form strong, RXB = 0.78–0.83, halogen bonds with dioxane oxygen, pyridine nitrogen and a bromide anion in tetraproropyl ammonium bromide resulting in deep cavity cavitand structures.

Confinement inside a Crystalline Sponge Induces Pyrrole To Form N−H⋅⋅⋅π Bonded Tetramers

Based on the DFT‐level calculated molecular volume (V mol ) of pyrrole and its liquid density, pyrrole manifests the highest liquid density coefficient LD c (defined as [V mol • density • 0.6023]/FW) value of 0.7. Normal liquids have LD c < 0.63. This very high LD c is due to the strong N‐H … π interactions in solution and hence pyrrole can be considered to be a pseudo‐crystalline liquid. When trapped inside the confined space of the crystalline sponge a reorientation of the N‐H … π interaction is observed leading to specific cyclic N‐H … π tetramers and N‐H … π dimers, verified by single crystal X‐ray crystallographic and computational methods. These tetramers are of the same size as four …

Stacking of Sterically Congested Trifluoromethylated Aromatics in their Crystals – The Role of Weak F···π or F···F Contacts

European journal of organic chemistry : EurJOC 2020(38), 6073-6077 (2020). doi:10.1002/ejoc.202001008

N-Alkyl Ammonium Resorcinarene Salts as High-Affinity Tetravalent Chloride Receptors.

N-Alkyl ammonium resorcinarene salts (NARYs, Y=triflate, picrate, nitrate, trifluoroacetates and NARBr) as tetravalent receptors, are shown to have a strong affinity for chlorides. The high affinity for chlorides was confirmed from a multitude of exchange experiments in solution (NMR and UV/Vis), gas phase (mass spectrometry), and solid-state (X-ray crystallography). A new tetra-iodide resorcinarene salt (NARI) was isolated and fully characterized from exchange experiments in the solid-state. Competition experiments with a known monovalent bis-urea receptor (5) with strong affinity for chloride, reveals these receptors to have a much higher affinity for the first two chlorides, a similar af…

Iodine Clathrated: A Solid‐State Analogue of the Iodine–Starch Complex

Co-crystallizing iodine with a simple dicationic salt (1,8-diammoniumoctane chloride) results in the clathration of the iodine (I2 ) molecules inside trigonal and hexagonal helical channels of the crystal lattice with 72 wt % overall I2 loading. The I2 inside the bigger trigonal channel forms a I-I⋅⋅⋅I-I⋅⋅⋅I-I halogen-bonded infinite helical chain, while the I2 in the smaller hexagonal channel is disordered. In both channels the I2 interaction with the channel wall happens through I-I⋅⋅⋅Cl- halogen bonds. The helical channels in the crystal lattice are constructed via the strong charge-assisted H2 N+ H⋅⋅⋅Cl- hydrogen bonds between the dications and the chloride anions. The structure shows a…

Iodine Clathrated : A Solid-State Analog of the Iodine-Starch Complex

Co-crystallizing iodine with a simple dicationic salt (1,8- diammoniumoctane chloride) results in the clathration of the iodine (I2) molecules inside trigonal and hexagonal helical channels of the crystal lattice with 72 wt% overall I2 loading. The I2 inside the bigger trigonal channel forms a I-I•••I-I•••I-I halogen-bonded infinite helical chain, while the I2 in the smaller hexagonal channel is disordered. In both channels the I2 interaction with the channel wall happens through I-I•••Cl- halogen bonds. The helical channels in the crystal lattice are constructed via the strong charge-assisted H2N+ -H•••Cl- hydrogen bonds between the dications and the chloride anions. The structure shows a …

Synthesis of tetrahalide dianions directed by crystal engineering

CrystEngComm 17(35), 6641-6645(2015). doi:10.1039/C5CE01288K

Anion-Exchange Properties of Trifluoroacetate and Triflate Salts of N-Alkylammonium Resorcinarenes

The synthesis of N-benzyl- and N-cyclohexylammonium resorcinarene trifluoroacetate (TFA) and triflate (OTf) salt receptors was investigated. Solid-state analysis by single-crystal X-ray diffraction revealed that the N-alkylammonium resorcinarene salts (NARSs) with different upper substituents had different cavity sizes and different affinities for anions. Anion-exchange experiments by mixing equimolar amounts of N-benzylammonium resorcinarene trifluoroacetate and N-cyclohexylammonium resorcinarene triflate, as well as N-benzylammonium resorcinarene triflate and N-cyclohexylammonium resorcinarene trifluoroacetate showed that the NARS with flexible benzyl groups preferred the larger OTf anion…

Polyoxygenated Cyclohexenes and Other Constituents of Cleistochlamys kirkii Leaves.

Thirteen new metabolites, including the polyoxygenated cyclohexene derivatives cleistodiendiol (1), cleistodienol B (3), cleistenechlorohydrins A (4) and B (5), cleistenediols A-F (6-11), cleistenonal (12), and the butenolide cleistanolate (13), 2,5-dihydroxybenzyl benzoate (cleistophenolide, 14), and eight known compounds (2, 15-21) were isolated from a MeOH extract of the leaves of Cleistochlamys kirkii. The purified metabolites were identified by NMR spectroscopic and mass spectrometric analyses, whereas the absolute configurations of compounds 1, 17, and 19 were established by single-crystal X-ray diffraction. The configuration of the exocyclic double bond of compound 2 was revised base…

A conformationally adaptive macrocycle : conformational complexity and host–guest chemistry of zorb[4]arene

Large amplitude conformational change is one of the features of biomolecular recognition and is also the basis for allosteric effects and signal transduction in functional biological systems. However, synthetic receptors with controllable conformational changes are rare. In this article, we present a thorough study on the host–guest chemistry of a conformationally adaptive macrocycle, namely per-O-ethoxyzorb[4]arene (ZB4). Similar to per-O-ethoxyoxatub[4]arene, ZB4 is capable of accommodating a wide range of organic cations. However, ZB4 does not show large amplitude conformational responses to the electronic substituents on the guests. Instead of a linear free-energy relationship, ZB4 foll…

N-Alkyl ammonium resorcinarene salts: multivalent halogen-bonded deep-cavity cavitands

N-Cyclohexyl ammonium resorcinarene halides, stabilized by an intricate array of hydrogen bonds in a cavitand-like assembly, form multivalent halogen-bonded deep-cavity cavitands with perfluoroiodobenzenes. As observed from the macromolar to infinite concentration range through crystal growth and single crystal X-ray analyses, four 1,4-diiodotetrafluorobenzenes form moderate halogen bonds with the bromides of the N-cyclohexyl ammonium resorcinarene bromides leading to a deep-cavity cavitand-like structure. In this assembly, the N-cyclohexyl ammonium resorcinarene bromide also acts as a guest and sits in the upper cavity of the assembly interacting with the 1,4-diiodotetrafluorobenzene throu…

Organic Polyradicals as Redox Mediators: Effect of Intramolecular Radical Interactions on Their Efficiency

The spin–spin interactions between unpaired electrons in organic (poly)radicals, especially nitroxides, are largely investigated and are of crucial importance for their applications in areas such as organic magnetism, molecular charge transfer, or multiple spin labeling in structural biology. Recently, 2,2,6,6-tetramethylpiperidinyloxyl and polymers functionalized with nitroxides have been described as successful redox mediators in several electrochemical applications; however, the study of spin–spin interaction effect in such an area is absent. This communication reports the preparation of a novel family of discrete polynitroxide molecules, with the same number of radical units but differe…

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…

Concerted Halogen-Bonded Networks with N-Alkyl Ammonium Resorcinarene Bromides: From Dimeric Dumbbell to Capsular Architectures

N-Alkyl ammonium resorcinarene bromides and 1,4-diiodooctafluorobutane via multiple intermolecular halogen bonds (XB) form different exotic supramolecular architectures through subtle changes of the upper rim substituents. Dimeric dumbbell-like assembly with encapsulated guest molecules is generated with N-benzyl substituents. The N-hexyl groups engender an XB-induced polymeric pseudocapsule and an XB-induced dimeric capsule with entrapped 1,4-dioxane guest molecules. The N-propyl and N-cyclohexyl groups generate deep cavity cavitands. The deep cavity cavitands possess cavities for self-inclusion leading to polymeric herringbone arrangement in one direction and that pack into 3D polymeric a…

N-(6-Methylpyridin-2-yl)mesitylenesulfonamide and acetic acid--a salt, a cocrystal or both?

In the solid obtained fromN-(6-methylpyridin-2-yl)mesitylenesulfonamide and acetic acid, the constituents interactviatwo N—H...O hydrogen bonds. The H atom situated in one of these short contacts is disordered over two positions: one of these positions is formally associated with an adduct of the neutral sulfonamide molecule and the neutral acetic acid molecule, and corresponds to a cocrystal, while the alternative site is associated with salt formation between a protonated sulfonamide molecule and deprotonated acetic acid molecule. Site-occupancy refinements and electron densities from difference Fourier maps suggest a trend with temperature, albeit of limited significance; the cocrystal i…

Water Structure Recovery in Chaotropic Anion Recognition: High-Affinity Binding of Dodecaborate Clusters to γ-Cyclodextrin

Dodecaborate anions of the type B12X12(2-) and B12X11Y(2-) (X=H, Cl, Br, I and Y=OH, SH, NH3(+), NR3(+)) form strong (K(a) up to 10(6) L mol(-1), for B12Br12(2-)) inclusion complexes with γ-cyclodextrin (γ-CD). The micromolar affinities reached are the highest known for this native CD. The complexation exhibits highly negative enthalpies (up to -25 kcal mol(-1)) and entropies (TΔS up to -18.4 kcal mol(-1), both for B12I12(2-)), which position these guests at the bottom end of the well-known enthalpy-entropy correlation for CDs. The high driving force can be traced back to a chaotropic effect, according to which chaotropic anions have an intrinsic affinity to hydrophobic cavities in aqueous …

N-Cinnamoyltetraketide Derivatives from the Leaves of Toussaintia orientalis

Seven N-cinnamoyltetraketides (1−7), including the new Ztoussaintine E (2), toussaintine F (6), and toussaintine G (7), were isolated from the methanol extract of the leaves of Toussaintia orientalis using column chromatography and HPLC. The configurations of E-toussaintine E (1) and toussaintines A (3) and D (5) are revised based on single-crystal X-ray diffraction data from racemic crystals. Both the crude methanol extract and the isolated constituents exhibit antimycobacterial activities (MIC 83.3−107.7 μM) against the H37Rv strain of Mycobacterium tuberculosis. Compounds 1, 3, 4, and 5 are cytotoxic (ED50 15.3−105.7 μM) against the MDA-MB-231 triple negative aggressive breast cancer cel…

Probing the guest-binding preference of three structurally similar and conformationally adaptive macrocycles.

A hybrid macrocycle was synthesized by combining the repeat units in oxatub[4]arene and zorb[4]arene, and its recognition behavior and conformational analysis were studied. Three structurally similar and conformationally adaptive macrocycles show different guest-binding selectivities and preferences even in a complex mixture containing three macrocycles and three guests.

A New Benzopyranyl Cadenane Sesquiterpene and Other Antiplasmodial and Cytotoxic Metabolites from Cleistochlamys kirkii

Phytochemical investigations of ethanol root bark and stem bark extracts of Cleistochlamys kirkii (Benth.) Oliv. (Annonaceae) yielded a new benzopyranyl cadinane-type sesquiterpene (cleistonol, 1) alongside 12 known compounds (2&ndash

Base-assisted synthesis of 4-pyridinate gold(I) metallaligands: a study of their use in self-assembly reactions

Made available in DSpace on 2021-06-25T12:16:58Z (GMT). No. of bitstreams: 0 Previous issue date: 2021-05-06 Ministerio de Economia y Competitividad (MINECO/FEDER) of Spain Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) The synthesis of di- and tritopic gold(I) metallaligands of the type [(Au4-py)(2)(mu(2)-diphosphane)] (diphosphane = bis(diphenylphosphanyl)isopropane or dppip (1), 1,2-bis(diphenylphosphanyl)ethane or dppe (2), 1,3-bis(diphenylphosphanyl)propane or dppp (3) and 1,4-bis(diphenylphosphanyl)butane or dppb (4)) and [(Au4-py)(3)(mu(3)-triphosphane)] (triphosphane = 1,1,1-tris(diphenylphosph…

Synthesis of 7-Pentafluorophenyl-1H-indole: An Anion Receptor for Anion–π Interactions

7-Pentafluorophenyl-1H-indole has the potential to be a key compound for the investigation of anion–π interactions in solution. Unfortunately, it was not possible to obtain it by aryl–aryl coupling reaction. Finally, it has been prepared by Bartoli indole synthesis. The key compound as well as analogues were submitted to preliminary studies of anion binding. Single crystals of two key receptors were obtained.

Connecting Electron-Deficient and Electron-Rich Aromatics to Support Intermolecular Interactions in Crystals

Five compounds bearing electron-deficient pentafluorophenyl as well as electron-rich (salicylate or indole) aromatic moieties connected by amide or ester linkages were investigated by X-ray diffraction. In the crystals, various interactions (π–π, lone pair–π) between the different aromatic units are important structure controlling factors in addition to the stronger inter- or intramolecular hydrogen bonds induced by the amide and ester moieties. The hydrogen bonding leads to polymeric and macrocyclic assembly of the molecular building blocks.

Naphthalene Derivatives from the Roots of Pentas parvifolia and Pentas bussei

The phytochemical investigation of the CH2Cl2/MeOH (1:1) extract of the roots of Pentas parvifolia led to the isolation of three new naphthalenes, parvinaphthols A (1), B (2), and C (3), two known anthraquinones, and five known naphthalene derivatives. Similar investigation of the roots of Pentas bussei afforded a new polycyclic naphthalene, busseihydroquinone E (4), a new 2,2'-binaphthralenyl-1,1'-dione, busseihydroquinone F (5), and five known naphthalenes. All purified metabolites were characterized by NMR and MS data analyses, whereas the absolute configurations of 3 and 4 were determined by single-crystal X-ray diffraction studies. The E-geometry of compound 5 was supported by DFT-base…

Dimeric resorcinarene salt capsules with very tight encapsulation of anions and guest molecules

Crystallization of N-cyclohexyl ammonium resorcinarene triflate from methanol results in a dimeric capsule capable of trapping two triflate anions and two methanol molecules within a 341 A3 cavity while with 1,4-dioxane as a guest it forms a new larger dimeric capsule with volume of 679 A3 encapsulating four 1,4-dioxane and four water molecules, resulting in packing coefficients of 0.75 and 0.67, respectively.

Isoflavones and Rotenoids from the Leaves of Millettia oblata ssp. teitensis

A new isoflavone, 8-prenylmilldrone (1), and four new rotenoids, oblarotenoids A−D (2−5), along with nine known compounds (6−14), were isolated from the CH2Cl2/CH3OH (1:1) extract of the leaves of Millettia oblata ssp. teitensis by chromatographic separation. The purified compounds were identified by NMR spectroscopic and mass spectrometric analyses, whereas the absolute configurations of the rotenoids were established on the basis of chiroptical data and in some cases by single-crystal X-ray crystallography. Maximaisoflavone J (11) and oblarotenoid C (4) showed weak activity against the human breast cancer cell line MDA-MB-231 with IC50 values of 33.3 and 93.8 μM, respectively. peerReviewed

Guest-Induced Folding of the N-Benzyl Substituents in an Ammonium Resorcinarene Chloride and the Formation of a Halogen-Bonded Dimer of Capsules

In methanol, N-benzyl ammonium resorcinarene chloride (Bn-NARCl) crystallizes as a solvate with the benzyl groups oriented in an open flower-like manner parallel to the cation–anion seam. 1,4-Dioxane as guest triggers a “semi-closed” single-molecule capsule with two benzyl “arms” enclosing the guest. The introduction of halogen bond (XB) donor 1,4-diiodoperfluorobutane (1,4-DIOFB) additionally folds the remaining two benzyl arms thus resulting in a fully closed capsule. Two 1,4-DIOFB molecules bridge two such Bn-NARCl capsules, forming a 2:2:2 XB held dimeric assembly of single-molecule capsules. The peculiar behavior was not observed in the bromide analog under similar experimental conditi…

Connecting Electron-Deficient and Electron-Rich Aromatics to Support Intermolecular Interactions in Crystals (Eur. J. Org. Chem. 15/2015)

Rücktitelbild: Water Structure Recovery in Chaotropic Anion Recognition: High-Affinity Binding of Dodecaborate Clusters to γ-Cyclodextrin (Angew. Chem. 23/2015)

Au25(SEt)18 a nearly naked thiolate-protected Au25 cluster Struct. analysis by single crystal X-ray crystallograp. and electron nuclear double res

X-ray crystallography has been fundamental in discovering fine structural features of ultrasmall gold clusters capped by thiolated ligands. For still unknown structures, however, new tools capable of providing relevant structural information are sought. We prepared a 25-gold atom nanocluster protected by the smallest ligand ever used, ethanethiol. This cluster displays the electrochemistry, mass spectrometry, and UV-vis absorption spectroscopy features of similar Au25 clusters protected by 18 thiolated ligands. The anionic and the neutral form of Au25(SEt)18 were fully characterized by (1)H and (13)C NMR spectroscopy, which confirmed the monolayer's properties and the paramagnetism of neutr…

A Halogen-Bonded Dimeric Resorcinarene Capsule.

Iodine (I2) acts as a bifunctional halogen-bond donor connecting two macrocyclic molecules of the bowl-shaped halogen-bond acceptor, N-cyclohexyl ammonium resorcinarene chloride 1, to form the dimeric capsule [(1,4-dioxane)3@1(2)(I2)2]. The dimeric capsule is constructed solely through halogen bonds and has a single cavity (V=511 Å(3)) large enough to encapsulate three 1,4-dioxane guest molecules.

Effects of side chains of oxatub[4]arene on its conformational interconversion, molecular recognition and macroscopic self-assembly.

A series of oxatub[4]arenes with different alkyl side chains have been synthesized. The conformational interconversion, molecular recognition and macroscopic self-assembly behaviour of oxatub[4]arene derivatives were investigated. The difference in side chains slightly changes the binding affinities, but results in different self-assembly morphologies at the solid state.

Electrocrystallization of Monolayer-Protected Gold Clusters : Opening the Door to Quality, Quantity, and New Structures

Thiolate-protected metal clusters are materials of ever-growing importance in fundamental and applied research. Knowledge of their single-crystal X-ray structures has been instrumental to enable advanced molecular understanding of their intriguing properties. So far, however, a general, reliable, chemically clean approach to prepare single crystals suitable for accurate crystallographic analysis was missing. Here we show that single crystals of thiolate-protected clusters can be grown in large quantity and very high quality by electrocrystallization. This method relies on the fact that charged clusters display a higher solubility in polar solvents than their neutral counterparts. Nucleation…

Binding Profiles of Self-Assembled Supramolecular Cages from ESI-MS Based Methodology

Confined molecular environments have peculiar characteristics that make their properties unique in the field of biological and chemical sciences. In recent years, advances in supramolecular capsule and cage synthesis have presented the possibility to interpret the principles behind their self‐assembly and functions, which has led to new molecular systems that display outstanding properties in molecular recognition and catalysis. Herein, we report a rapid method based on ESI‐MS to determine the binding profiles for linear saturated dicarboxylic acids in a series of different cages. The cages were obtained by self‐assembly of modified tris(pyridylmethyl)amine (TPMA) complexes and diamines cho…

CF3: An Electron-Withdrawing Substituent for Aromatic Anion Acceptors? “Side-On” versus “On-Top” Binding of Halides

The ability of multiple CF3 -substituted arenes to act as acceptors for anions is investigated. The results of quantum-chemical calculations show that a high degree of trifluoromethyl substitution at the aromatic ring results in a positive quadrupole moment. However, depending on the polarizability of the anion and on the substitution at the arene, three different modes of interaction, namely Meisenheimer complex, side-on hydrogen bonding, or anion-π interaction, can occur. Experimentally, the side-on as well as a η(2) -type π-complex are observed in the crystal, whereas in solution only side-on binding is found.

Cooperative Binding of Divalent Diamides by N-Alkyl Ammonium Resorcinarene Chlorides

N-Alkyl ammonium resorcinarene chlorides, stabilized by an intricate array of hydrogen bonds leading to a cavitand-like structure, bind amides. The molecular recognition occurs through intermolecular hydrogen bonds between the carbonyl oxygen and the amide hydrogen of the guests and the cation-anion circular hydrogen-bonded seam of the hosts, as well as through CH⋅⋅⋅π interactions. The N-alkyl ammonium resorcinarene chlorides cooperatively bind a series of di-acetamides of varying spacer lengths ranging from three to seven carbons. Titration data fit either a 1:1 or 2:1 binding isotherm depending on the spacer lengths. Considering all the guests possess similar binding motifs, the first bin…

A Supramolecular Chiral Auxiliary Approach: “Remote Control ”of Stereochemistry at a Hierarchically Assembled Dimeric Helicate

Dimeric hierarchically-assembled titanium(IV) helicates are in solvent-dependent equilibrium with the corresponding monomers. Statistically formed mixtures of such complexes bearing chiral stereocontrolling ligands and achiral diene-substituted ligands show high diastereoselectivity and reasonable enantioselectivity in the Diels-Alder reaction with maleimides if the reaction proceeds with the dimer but not with the monomer. Thus, solvent dependent switching between the monomer and dimer enables on/off switching of the enantioselectivity.

Bis-urea macrocycles with a deep cavity

A magnetic look into the protecting layer of Au25 clusters

The field of molecular metal clusters protected by organothiolates is experiencing a very rapid growth. So far, however, a clear understanding of the fine interactions between the cluster core and the capping monolayer has remained elusive, despite the importance of the latter in interfacing the former to the surrounding medium. Here, we describe a very sensitive methodology that enables comprehensive assessment of these interactions. Pulse electron nuclear double resonance (ENDOR) was employed to study the interaction of the unpaired electron with the protons of the alkanethiolate ligands in four structurally related paramagnetic Au25(SR)0 18 clusters (R ¼ ethyl, propyl, butyl, 2-methylpro…

Hierarchical Ordering in Ternary Co-Crystals of C60, N-Benzyl Ammonium Resorcinarene Bromide and Solvent Molecules

Co-crystallization of C60 together with an N-benzyl ammonium resorcinarene bromide from toluene:1,2-dichloroethane mixture results in ternary co-crystals where the modulated C60 lattice entraps dimeric resorcinarene assemblies, which, in turn, have 149 and 280 A3 cavities filled with 1,2-dichloroethane molecules.

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…

Gold Nanowired: A Linear (Au25)n Polymer from Au25 Molecular Clusters

Au25(SR)18 has provided fundamental insights into the properties of clusters protected by monolayers of thiolated ligands (SR). Because of its ultrasmall core, 1 nm, Au25(SR)18 displays molecular behavior. We prepared a Au25 cluster capped by n-butanethiolates (SBu), obtained its structure by single-crystal X-ray crystallography, and studied its properties both experimentally and theoretically. Whereas in solution Au25(SBu)18(0) is a paramagnetic molecule, in the crystal it becomes a linear polymer of Au25 clusters connected via single Au-Au bonds and stabilized by proper orientation of clusters and interdigitation of ligands. At low temperature, [Au25(SBu)18(0)]n has a nonmagnetic ground s…

Halogen-bonded solvates of tetrahaloethynyl cavitands

The formation and structures of halogen-bonded solvates of three different tetrahaloethynyl cavitands with acetone, chloroform, acetonitrile, DMF and DMSO were prepared and investigated. The inclusion and host–guest behaviour of the resorcinarene cavitands was found to be highly dependent on the flexibility of the ethylene-bridging unit.

Back Cover: Water Structure Recovery in Chaotropic Anion Recognition: High-Affinity Binding of Dodecaborate Clusters to γ-Cyclodextrin (Angew. Chem. Int. Ed. 23/2015)

Bamboo-like Chained Cavities and Other Halogen-Bonded Complexes from Tetrahaloethynyl Cavitands with Simple Ditopic Halogen Bond Acceptors

Halogen bonding provides a useful complement to hydrogen bonding and metal-coordination as a tool for organizing supramolecular systems. Resorcinarenes, tetrameric bowl-shaped cavitands, have been previously shown to function as efficient scaffolds for generating dimeric capsules in both solution and solid-phase, and complicated one-, two-, and three-dimensional frameworks in the solid phase. Tetrahaloethynyl resorcinarenes (bromide and iodide) position the halogen atoms in a very promising “crown-like” orientation for acting as organizing halogen-bond donors to help build capsules and higher-order networks. Symmetric divalent halogen bond acceptors including bipyridines, 1,4-dioxane, and 1…

Flavonoids from Erythrina schliebenii

Prenylated and O-methylflavonoids including one new pterocarpan (1), three new isoflavones (2–4), and nineteen known natural products (5–23) were isolated and identified from the root, stem bark, and leaf extracts of Erythrina schliebenii. The crude extracts and their constituents were evaluated for antitubercular activity against Mycobacterium tuberculosis (H37Rv strain), showing MICs of 32–64 μg mL–1 and 36.9–101.8 μM, respectively. Evaluation of their toxicity against the aggressive human breast cancer cell line MDA-MB-231 indicated EC50 values of 13.0–290.6 μM (pure compounds) and 38.3 to >100 μg mL–1 (crude extracts).

Synthesis of Quinoline-Based Anion Receptors and Preliminary Anion Binding Studies with Selected Derivatives

Six quinoline-based anion receptors were designed, prepared, and characterized, among which the crystal structure of an indole derivative was obtained. Selected receptors were tested for the recognition of halide anions in solution and showed some selectivity of chloride over bromide and iodide.

N-Alkyl ammonium resorcinarene salts: multivalent halogen-bonded deep-cavity cavitands

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…

N-Alkyl ammonium resorcinarene polyiodides

Four N-alkyl ammonium resorcinarene halides incorporating polyiodides were obtained and structurally analyzed by single crystal X-ray crystallography. The unexpected formation of triiodides and pentaiodide anions in these structures was assumed to be the result of the heterolytic dissociation of molecular iodine (I2) in the presence of electron donors in the N-alkyl ammonium resorcinarene halide system, from which I− further binds one or two I2 molecules resulting in I3− or I5− species, respectively.

From isolated 1H-pyrazole cryptand anion receptors to hybrid inorganic-organic 1D helical polymeric anion receptors

We report a novel 1-D helical coordination polymer formed by protonated polyamine 1H-pyrazole cryptands interconnected by Cu2+ metal ions that are able to encapsulate anionic species behaving as a multianion receptor. Switching from a monomeric receptor to a polymeric receptor is activated by metal ions and pH.

Guest-Induced Folding and Self-Assembly of Conformationally Adaptive Macrocycles into Nanosheets and Nanotubes

A conformationally adaptive macrocycle is presented, namely zorb[4]arene, which exists in multiple conformations in the uncomplexed state. The binding cavity of zorb[4]arene is concealed, either due to a collapsed conformation or by self-inclusion. The zorb[4]arene with long alkyl chains manifests itself with surprisingly low melting point and thus exist as an oil at room temperature. Binding of a guest molecule induces the folding and conformational rigidity of zorb[4]arene and leads to well-defined three-dimensional structures, which can further self-assemble into nanosheets or nanotubes upon solvent evaporation, depending on guest molecules and the conformations they can induce.

Counterion influence on the N–I–N halogen bond

A detailed investigation of the influence of counterions on the [N–I–N]+ halogen bond in solution, in the solid state and in silico is presented. Translational diffusion coefficients indicate close attachment of counterions to the cationic, three-center halogen bond in dichloromethane solution. Isotopic perturbation of equilibrium NMR studies performed on isotopologue mixtures of regioselectively deuterated and nondeuterated analogues of the model system showed that the counterion is incapable of altering the symmetry of the [N–I–N]+ halogen bond. This symmetry remains even in the presence of an unfavorable geometric restraint. A high preference for the symmetric geometry was found also in …

Bringing a Molecular Plus One: Synergistic Binding Creates Guest-Mediated Three-Component Complexes

Cethyl-2-methylresorcinarene (A), pyridine (B), and a set of 10 carboxylic acids (Cn) associate to form A·B·Cn ternary assemblies with 1:1:1 stoichiometry, representing a useful class of ternary systems where the guest mediates complex formation between the host and a third component. Although individually weak in solution, the combined strength of the multiple noncovalent interactions organizes the complexes even in a highly hydrogen-bond competing methanol solution, as explored by both experimental and computational methods. The interactions between A·B and Cn are dependent on the pKa values of carboxylic acids. The weak interactions between A and C further reinforce the interactions betw…

Counterion influence on the N–I–N halogen bond† †Electronic supplementary information (ESI) available: Experimental details of synthesis, compound characterisation, IPE NMR measurements, computational and crystallographic procedures, and crystal data for 1-Ag/I to 7-Ag/I, and 12-Ag. CCDC 1045981–1045995. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc01053e Click here for additional data file. Click here for additional data file.

Counterions influence three-center halogen bonds differently than coordination bonds of transition metals.

Halogen bonding and host–guest chemistry between N-alkylammonium resorcinarene halides, diiodoperfluorobutane and neutral guests

Single crystal X-ray structures of halogen-bonded assemblies formed between host N-hexylammonium resorcinarene bromide (1) or N-cyclohexylammonium resorcinarene chloride (2), and 1,4-diiodooctafluorobutane and accompanying small solvent guests (methanol, acetonitrile and water) are presented. The guests’ inclusion affects the geometry of the cavity of the receptors 1 and 2, while the divalent halogen bond donor 1,4-diiodooctafluorobutane determines the overall nature of the halogen bond assembly. The crystal lattice of 1 contains two structurally different dimeric assemblies A and B, formally resulting in the mixture of a capsular dimer and a dimeric pseudo-capsule. 1H and 19F NMR analyses …

Bis-urea macrocycles with a deep cavity.

Two configurational isomers of bis-urea macrocycles have been synthesized, and their neutral molecule recognition was studied by X-ray crystallography and (1)H NMR experiments. Cooperative action between the deep cavity and the urea groups and the influence of dipole alignments on molecular recognition are discussed.

Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: the effect of size and charge concentration

The binding of different categories of alkyl ammonium (secondary and tertiary mono- and di-ammonium) salts with resorcinarenes and a pyrogallarene through weak interactions was analysed in all phases. 1H NMR spectroscopy and electrospray ionisation mass spectrometry were utilized in analysing the complexes in solution and in the gas phase, respectively. The 1H NMR titration studies in methanol-d4 reveal that the association constants for the 1:1 complexes vary according to the electronic properties of the hosts as well as the size, geometric orientation and charge concentration of the guest cations with binding constants of up to 950 M−1 in some cases. Mass spectrometry reveals 1:1 monomeri…

N-Alkyl Ammonium Resorcinarene Chloride Receptors for Guest Binding in Aqueous Environment

Host systems with guest binding ability in water and/or biological fluids are a current challenge in supramolecular host–guest chemistry. Here we present the first syntheses of water-soluble N-ethanol ammonium resorcinarene chlorides (NARCls) with terminal hydroxyl groups at the upper rim. The NARCls possess deep cavities and are shown to bind a variety of guest molecules such as linear and cyclic alkanes, linear halogenated alkanes, and aromatic fluorophores (naphthalene, p-(phenylazo)phenol) in water through hydrophobic interactions, as well as 1,4-dioxane (a water soluble guest) via hydrogen bonds. The receptors are monomeric in aqueous media and form 1:1 host–guest complexes with bindin…

CCDC 1051388: Experimental Crystal Structure Determination

Related Article: Ngong Kodiah Beyeh, Fangfang Pan, Kari Rissanen|2015|Angew.Chem.,Int.Ed.|54|7303|doi:10.1002/anie.201501855

CCDC 1913149: Experimental Crystal Structure Determination

Related Article: Hongxin Chai, Zhi-Sheng Pan, Liu-Pan Yang, Shan He, Fangfang Pan, Kari Rissanen, Wei Jiang|2019|Chem.Commun.|55|7768|doi:10.1039/C9CC03341F

CCDC 1481997: Experimental Crystal Structure Determination

Related Article: Fangfang Pan, Ngong Kodiah Beyeh, Robin H. A. Ras, Kari Rissanen|2016|CrystEngComm|18|5724|doi:10.1039/C6CE01229A

CCDC 2051585: Experimental Crystal Structure Determination

Related Article: Mengling Wu, Junle Zhang, Liangqian Yuan, Kari Rissanen, Fangfang Pan|2021|Chem.-Eur.J.|27|9814|doi:10.1002/chem.202100087

CCDC 1417789: Experimental Crystal Structure Determination

Related Article: Guobao Huang, Zhenfeng He, Chen-Xi Cai, Fangfang Pan, Dingqiao Yang, Kari Rissanen, Wei Jiang|2015|Chem.Commun.|51|15490|doi:10.1039/C5CC06768E

CCDC 1045987: Experimental Crystal Structure Determination

Related Article: Michele Bedin, Alavi Karim, Marcus Reitti, Anna-Carin C. Carlsson, Filip Topić, Mario Cetina, Fangfang Pan, Vaclav Havel, Fatima Al-Ameri, Vladimir Sindelar, Kari Rissanen, Jürgen Gräfenstein, Máté Erdélyi|2015|Chemical Science|6|3746|doi:10.1039/C5SC01053E

CCDC 1045995: Experimental Crystal Structure Determination

Related Article: Michele Bedin, Alavi Karim, Marcus Reitti, Anna-Carin C. Carlsson, Filip Topić, Mario Cetina, Fangfang Pan, Vaclav Havel, Fatima Al-Ameri, Vladimir Sindelar, Kari Rissanen, Jürgen Gräfenstein, Máté Erdélyi|2015|Chemical Science|6|3746|doi:10.1039/C5SC01053E

CCDC 1938867: Experimental Crystal Structure Determination

Related Article: S. Maryamdokht Taimoory, Kwaku Twum, Mohadeseh Dashti, Fangfang Pan, Manu Lahtinen, Kari Rissanen, Rakesh Puttreddy, John F. Trant, Ngong Kodiah Beyeh|2020|J.Org.Chem.|85|5884|doi:10.1021/acs.joc.0c00220

CCDC 1045983: Experimental Crystal Structure Determination

Related Article: Michele Bedin, Alavi Karim, Marcus Reitti, Anna-Carin C. Carlsson, Filip Topić, Mario Cetina, Fangfang Pan, Vaclav Havel, Fatima Al-Ameri, Vladimir Sindelar, Kari Rissanen, Jürgen Gräfenstein, Máté Erdélyi|2015|Chemical Science|6|3746|doi:10.1039/C5SC01053E

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 1497772: Experimental Crystal Structure Determination

Related Article: Stephen S. Nyandoro, Joan J. E. Munissi, Amra Gruhonjic, Sandra Duffy, Fangfang Pan, Rakesh Puttreddy, John P. Holleran, Paul A. Fitzpatrick, Jerry Pelletier, Vicky M. Avery, Kari Rissanen, Máté Erdélyi|2017|J.Nat.Prod.|80|114|doi:10.1021/acs.jnatprod.6b00759

CCDC 955438: Experimental Crystal Structure Determination

Related Article: Zhan-Hu Sun, Markus Albrecht, Michael Giese, Fangfang Pan, Kari Rissanen|2014|Synlett|25|2075|doi:10.1055/s-0034-1378449

CCDC 1040204: Experimental Crystal Structure Determination

Related Article: Markus Albrecht, Yi Hai, Okan Köksal, Gerhard Raabe, Fangfang Pan, Arto Valkonen and Kari Rissanen|2016|Chem.-Eur.J.|22|6596|doi:10.1002/chem.201600249

CCDC 1045988: Experimental Crystal Structure Determination

Related Article: Michele Bedin, Alavi Karim, Marcus Reitti, Anna-Carin C. Carlsson, Filip Topić, Mario Cetina, Fangfang Pan, Vaclav Havel, Fatima Al-Ameri, Vladimir Sindelar, Kari Rissanen, Jürgen Gräfenstein, Máté Erdélyi|2015|Chemical Science|6|3746|doi:10.1039/C5SC01053E

CCDC 2009942: Experimental Crystal Structure Determination

Related Article: Mengling Wu, Junle Zhang, Liangqian Yuan, Kari Rissanen, Fangfang Pan|2021|Chem.-Eur.J.|27|9814|doi:10.1002/chem.202100087

CCDC 1556027: Experimental Crystal Structure Determination

Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, Mario Cetina, John F. Trant, Robin H. A. Ras, Kari Rissanen|2017|CrystEngComm|19|5223|doi:10.1039/C7CE01118K

CCDC 1045990: Experimental Crystal Structure Determination

Related Article: Michele Bedin, Alavi Karim, Marcus Reitti, Anna-Carin C. Carlsson, Filip Topić, Mario Cetina, Fangfang Pan, Vaclav Havel, Fatima Al-Ameri, Vladimir Sindelar, Kari Rissanen, Jürgen Gräfenstein, Máté Erdélyi|2015|Chemical Science|6|3746|doi:10.1039/C5SC01053E

CCDC 1577176: Experimental Crystal Structure Determination

Related Article: Liu-Pan Yang, Fei Jia, Fangfang Pan, Zhi-Sheng Pan, Kari Rissanen, Wei Jiang|2017|Chem.Commun.|53|12572|doi:10.1039/C7CC07630D

CCDC 1401637: Experimental Crystal Structure Determination

Related Article: Fangfang Pan, N. Kodiah Beyeh, Kari Rissanen|2015|RSC Advances|5|57912|doi:10.1039/C5RA11905G

CCDC 984217: Experimental Crystal Structure Determination

Related Article: Tiziano Dainese, Sabrina Antonello, José A. Gascón, Fangfang Pan, Neranjan V. Perera, Marco Ruzzi, Alfonso Venzo, Alfonso Zoleo, Kari Rissanen, and Flavio Maran|2014|ACS Nano|8|3904|doi:10.1021/nn500805n

CCDC 1995537: Experimental Crystal Structure Determination

Related Article: Hai Yi, Markus Albrecht, Fangfang Pan, Arto Valkonen, Kari Rissanen|2020|Eur.J.Org.Chem.||6073|doi:10.1002/ejoc.202001008

CCDC 1488064: Experimental Crystal Structure Determination

Related Article: Fangfang Pan, Ngong Kodiah Beyeh, Robin H. A. Ras, Kari Rissanen|2016|Cryst.Growth Des.|16|6729|doi:10.1021/acs.cgd.6b01454

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 1429823: Experimental Crystal Structure Determination

Related Article: N. Kodiah Beyeh, Fangfang Pan, Sandip Bhowmik, Toni Mäkelä, Robin H. A. Ras, Kari Rissanen|2016|Chem.-Eur.J.|22|1355|doi:10.1002/chem.201504514

CCDC 1429824: Experimental Crystal Structure Determination

Related Article: N. Kodiah Beyeh, Fangfang Pan, Sandip Bhowmik, Toni Mäkelä, Robin H. A. Ras, Kari Rissanen|2016|Chem.-Eur.J.|22|1355|doi:10.1002/chem.201504514

A conformationally adaptive macrocycle: conformational complexity and host–guest chemistry of zorb[4]arene

Large amplitude conformational change is one of the features of biomolecular recognition and is also the basis for allosteric effects and signal transduction in functional biological systems. However, synthetic receptors with controllable conformational changes are rare. In this article, we present a thorough study on the host–guest chemistry of a conformationally adaptive macrocycle, namely per-O-ethoxyzorb[4]arene (ZB4). Similar to per-O-ethoxyoxatub[4]arene, ZB4 is capable of accommodating a wide range of organic cations. However, ZB4 does not show large amplitude conformational responses to the electronic substituents on the guests. Instead of a linear free-energy relationship, ZB4 foll…

CCDC 1488067: Experimental Crystal Structure Determination

Related Article: Fangfang Pan, Ngong Kodiah Beyeh, Robin H. A. Ras, Kari Rissanen|2016|Cryst.Growth Des.|16|6729|doi:10.1021/acs.cgd.6b01454

CCDC 1429822: Experimental Crystal Structure Determination

Related Article: N. Kodiah Beyeh, Fangfang Pan, Sandip Bhowmik, Toni Mäkelä, Robin H. A. Ras, Kari Rissanen|2016|Chem.-Eur.J.|22|1355|doi:10.1002/chem.201504514

CCDC 1938870: Experimental Crystal Structure Determination

Related Article: S. Maryamdokht Taimoory, Kwaku Twum, Mohadeseh Dashti, Fangfang Pan, Manu Lahtinen, Kari Rissanen, Rakesh Puttreddy, John F. Trant, Ngong Kodiah Beyeh|2020|J.Org.Chem.|85|5884|doi:10.1021/acs.joc.0c00220

CCDC 1986124: Experimental Crystal Structure Determination

Related Article: Elena Badetti, Vega Lloveras, Emanuele Amadio, Rosalia Di Lorenzo, Mara Olivares-Marín, Alvaro Y. Tesio, Songbai Zhang, Fangfang Pan, Kari Rissanen, Jaume Veciana, Dino Tonti, Jose Vidal-Gancedo, Cristiano Zonta, Giulia Licini|2020|ACS Applied Materials and Interfaces|12|45968|doi:10.1021/acsami.0c09386

CCDC 1938871: Experimental Crystal Structure Determination

Related Article: S. Maryamdokht Taimoory, Kwaku Twum, Mohadeseh Dashti, Fangfang Pan, Manu Lahtinen, Kari Rissanen, Rakesh Puttreddy, John F. Trant, Ngong Kodiah Beyeh|2020|J.Org.Chem.|85|5884|doi:10.1021/acs.joc.0c00220

CCDC 1061111: Experimental Crystal Structure Determination

Related Article: Tsegaye Deyou, Marco Makungu, Matthias Heydenreich, Fangfang Pan, Amra Gruhonjic, Paul A. Fitzpatrick, Andreas Koch, Solomon Derese, Jerry Pelletier, Kari Rissanen, Abiy Yenesew, and Máté Erdélyi|2017|J.Nat.Prod.|80|2060|doi:10.1021/acs.jnatprod.7b00255

CCDC 1040206: Experimental Crystal Structure Determination

Related Article: Markus Albrecht, Yi Hai, Okan Köksal, Gerhard Raabe, Fangfang Pan, Arto Valkonen and Kari Rissanen|2016|Chem.-Eur.J.|22|6596|doi:10.1002/chem.201600249

CCDC 1045984: Experimental Crystal Structure Determination

Related Article: Michele Bedin, Alavi Karim, Marcus Reitti, Anna-Carin C. Carlsson, Filip Topić, Mario Cetina, Fangfang Pan, Vaclav Havel, Fatima Al-Ameri, Vladimir Sindelar, Kari Rissanen, Jürgen Gräfenstein, Máté Erdélyi|2015|Chemical Science|6|3746|doi:10.1039/C5SC01053E

CCDC 1452468: Experimental Crystal Structure Determination

Related Article: Ngong Kodiah Beyeh, Fangfang Pan, Robin H. A. Ras|2016|Asian J.Org.Chem|5|1027|doi:10.1002/ajoc.201600187

CCDC 1045981: Experimental Crystal Structure Determination

Related Article: Michele Bedin, Alavi Karim, Marcus Reitti, Anna-Carin C. Carlsson, Filip Topić, Mario Cetina, Fangfang Pan, Vaclav Havel, Fatima Al-Ameri, Vladimir Sindelar, Kari Rissanen, Jürgen Gräfenstein, Máté Erdélyi|2015|Chemical Science|6|3746|doi:10.1039/C5SC01053E

CCDC 1556030: Experimental Crystal Structure Determination

Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, Mario Cetina, John F. Trant, Robin H. A. Ras, Kari Rissanen|2017|CrystEngComm|19|5223|doi:10.1039/C7CE01118K

CCDC 1040201: Experimental Crystal Structure Determination

Related Article: Markus Albrecht, Yi Hai, Okan Köksal, Gerhard Raabe, Fangfang Pan, Arto Valkonen and Kari Rissanen|2016|Chem.-Eur.J.|22|6596|doi:10.1002/chem.201600249

CCDC 1895019: Experimental Crystal Structure Determination

Related Article: Kari Rissanen, Fangfang Pan, Yingchun Chen, Siyu Li, Minzhi Jiang|2019|Chem.-Eur.J.|25|7485|doi:10.1002/chem.201901734

Bis-urea macrocycles with a deep cavity

Two bis-urea macrocycles with a deep cavity demonstrate an enzyme-like binding, and the influence of dipole alignments on molecular recognition.

CCDC 2000612: Experimental Crystal Structure Determination

Related Article: Montserrat Ferrer, Albert Gutiérrez, Manuel Martínez, Cristiana Da Silva, Adelino V. G. Netto, Laura Rodríguez, Guillermo Romo-Islas, Fangfang Pan, Kari Rissanen|2021|Dalton Trans.|50|8154|doi:10.1039/D1DT00402F

CCDC 1995533: Experimental Crystal Structure Determination

Related Article: Hai Yi, Markus Albrecht, Fangfang Pan, Arto Valkonen, Kari Rissanen|2020|Eur.J.Org.Chem.||6073|doi:10.1002/ejoc.202001008

CCDC 1439768: Experimental Crystal Structure Determination

Related Article: Fangfang Pan, Ngong Kodiah Beyeh, Stefania Bertella, Kari Rissanen|2016|Chem.Asian J.|11|782|doi:10.1002/asia.201501335

CCDC 1481998: Experimental Crystal Structure Determination

Related Article: Fangfang Pan, Ngong Kodiah Beyeh, Robin H. A. Ras, Kari Rissanen|2016|CrystEngComm|18|5724|doi:10.1039/C6CE01229A

CCDC 1995536: Experimental Crystal Structure Determination

Related Article: Hai Yi, Markus Albrecht, Fangfang Pan, Arto Valkonen, Kari Rissanen|2020|Eur.J.Org.Chem.||6073|doi:10.1002/ejoc.202001008

CCDC 1995534: Experimental Crystal Structure Determination

Related Article: Hai Yi, Markus Albrecht, Fangfang Pan, Arto Valkonen, Kari Rissanen|2020|Eur.J.Org.Chem.||6073|doi:10.1002/ejoc.202001008

CCDC 1937081: Experimental Crystal Structure Determination

Related Article: Stephen S. Nyandoro, Gasper Maeda, Joan J.E. Munissi, Amra Gruhonjic, Paul A. Fitzpatrick, Sofia Lindblad, Sandra Duffy, Jerry Pelletier, Fangfang Pan, Rakesh Puttreddy, Vicky M. Avery, Máté Erdélyi|2019|Molecules|24|2746|doi:10.3390/molecules24152746

CCDC 1452354: Experimental Crystal Structure Determination

Related Article: Negera Abdissa, Fangfang Pan, Amra Gruhonjic, Jürgen Gräfenstein, Paul A. Fitzpatrick, Göran Landberg, Kari Rissanen, Abiy Yenesew, Máté Erdélyi|2016|J.Nat.Prod.|79|2181|doi:10.1021/acs.jnatprod.6b00178

CCDC 1556033: Experimental Crystal Structure Determination

Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, Mario Cetina, John F. Trant, Robin H. A. Ras, Kari Rissanen|2017|CrystEngComm|19|5223|doi:10.1039/C7CE01118K

CCDC 1038851: Experimental Crystal Structure Determination

Related Article: N. Kodiah Beyeh, Arto Valkonen, Sandip Bhowmik, Fangfang Pan, K. Rissanen|2015|Org.Chem.Front.|2|340|doi:10.1039/C4QO00326H

CCDC 1006950: Experimental Crystal Structure Determination

Related Article: N. Kodiah Beyeh, Fangfang Pan, and Kari Rissanen|2014|Cryst.Growth Des.|14|6161|doi:10.1021/cg5014413

CCDC 1498874: Experimental Crystal Structure Determination

Related Article: Stephen S. Nyandoro, Joan J. E. Munissi, Msim Kombo, Clarence A. Mgina, Fangfang Pan, Amra Gruhonjic, Paul Fitzpatrick, Yu Lu, Bin Wang, Kari Rissanen, Máté Erdélyi|2017|J.Nat.Prod.|80|377|doi:10.1021/acs.jnatprod.6b00839

CCDC 1417790: Experimental Crystal Structure Determination

Related Article: Guobao Huang, Zhenfeng He, Chen-Xi Cai, Fangfang Pan, Dingqiao Yang, Kari Rissanen, Wei Jiang|2015|Chem.Commun.|51|15490|doi:10.1039/C5CC06768E

CCDC 1519225: Experimental Crystal Structure Determination

Related Article: Sabrina Antonello, Tiziano Dainese, Fangfang Pan, Kari Rissanen, Flavio Maran|2017|J.Am.Chem.Soc.|139|4168|doi:10.1021/jacs.7b00568

CCDC 1417020: Experimental Crystal Structure Determination

Related Article: Fangfang Pan, Ngong Kodiah Beyeh, and Kari Rissanen|2015|J.Am.Chem.Soc.|137|10406|doi:10.1021/jacs.5b06590

CCDC 983275: Experimental Crystal Structure Determination

Related Article: Javier Pitarch-Jarque, Raquel Belda, Laura García-España, José M. Llinares, FangFang Pan, Kari Rissanen, Pilar Navarro, Enrique García-España|2015|Dalton Trans.|44|7761|doi:10.1039/C5DT00763A

CCDC 1040203: Experimental Crystal Structure Determination

Related Article: Markus Albrecht, Yi Hai, Okan Köksal, Gerhard Raabe, Fangfang Pan, Arto Valkonen and Kari Rissanen|2016|Chem.-Eur.J.|22|6596|doi:10.1002/chem.201600249

CCDC 1036897: Experimental Crystal Structure Determination

Related Article: Markus Albrecht, Hai Yi, Fangfang Pan, Arto Valkonen and Kari Rissanen|2015|Eur.J.Org.Chem.|2015|3235|doi:10.1002/ejoc.201500175

CCDC 1030676: Experimental Crystal Structure Determination

Related Article: Javier Pitarch-Jarque, Raquel Belda, Laura García-España, José M. Llinares, FangFang Pan, Kari Rissanen, Pilar Navarro, Enrique García-España|2015|Dalton Trans.|44|7761|doi:10.1039/C5DT00763A

CCDC 1439767: Experimental Crystal Structure Determination

Related Article: Fangfang Pan, Ngong Kodiah Beyeh, Stefania Bertella, Kari Rissanen|2016|Chem.Asian J.|11|782|doi:10.1002/asia.201501335

CCDC 1013128: Experimental Crystal Structure Determination

Related Article: Zhanhu Sun, Markus Albrecht, Fangfang Pan, Michel Waringo|2015|Synthesis|47|861|doi:10.1055/s-0034-1379605

CCDC 1417051: Experimental Crystal Structure Determination

Related Article: Fangfang Pan, Ngong Kodiah Beyeh, and Kari Rissanen|2015|J.Am.Chem.Soc.|137|10406|doi:10.1021/jacs.5b06590

CCDC 1417021: Experimental Crystal Structure Determination

Related Article: Fangfang Pan, Ngong Kodiah Beyeh, and Kari Rissanen|2015|J.Am.Chem.Soc.|137|10406|doi:10.1021/jacs.5b06590

CCDC 998586: Experimental Crystal Structure Determination

Related Article: Marco De Nardi, Sabrina Antonello, De-en Jiang, Fangfang Pan, Kari Rissanen, Marco Ruzzi, Alfonso Venzo, Alfonso Zoleo, Flavio Maran|2014|ACS Nano|8|8505|doi:10.1021/nn5031143

CCDC 1045982: Experimental Crystal Structure Determination

Related Article: Michele Bedin, Alavi Karim, Marcus Reitti, Anna-Carin C. Carlsson, Filip Topić, Mario Cetina, Fangfang Pan, Vaclav Havel, Fatima Al-Ameri, Vladimir Sindelar, Kari Rissanen, Jürgen Gräfenstein, Máté Erdélyi|2015|Chemical Science|6|3746|doi:10.1039/C5SC01053E

CCDC 1453036: Experimental Crystal Structure Determination

Related Article: Mikhail Agrachev, Sabrina Antonello, Tiziano Dainese, José A. Gascón, Fangfang Pan, Kari Rissanen, Marco Ruzzi, Alfonso Venzo, Alfonso Zoleo, Flavio Maran|2016|Chemical Science|7|6910|doi:10.1039/C6SC03691K

CCDC 1574172: Experimental Crystal Structure Determination

Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, John F. Trant, Robin H. A. Ras, Kari Rissanen|2018|Cryst.Growth Des.|18|513|doi:10.1021/acs.cgd.7b01517

CCDC 1995535: Experimental Crystal Structure Determination

Related Article: Hai Yi, Markus Albrecht, Fangfang Pan, Arto Valkonen, Kari Rissanen|2020|Eur.J.Org.Chem.||6073|doi:10.1002/ejoc.202001008

CCDC 1481996: Experimental Crystal Structure Determination

Related Article: Fangfang Pan, Ngong Kodiah Beyeh, Robin H. A. Ras, Kari Rissanen|2016|CrystEngComm|18|5724|doi:10.1039/C6CE01229A

CCDC 1036896: Experimental Crystal Structure Determination

Related Article: Markus Albrecht, Hai Yi, Fangfang Pan, Arto Valkonen and Kari Rissanen|2015|Eur.J.Org.Chem.|2015|3235|doi:10.1002/ejoc.201500175

CCDC 1488066: Experimental Crystal Structure Determination

Related Article: Fangfang Pan, Ngong Kodiah Beyeh, Robin H. A. Ras, Kari Rissanen|2016|Cryst.Growth Des.|16|6729|doi:10.1021/acs.cgd.6b01454

CCDC 1438663: Experimental Crystal Structure Determination

Related Article: David Van Craen, Markus Albrecht, Gerhard Raabe, Fangfang Pan, Kari Rissanen|2016|Chem.-Eur.J.|22|3255|doi:10.1002/chem.201600158

CCDC 1452743: Experimental Crystal Structure Determination

Related Article: Ngong Kodiah Beyeh, Fangfang Pan, Robin H. A. Ras|2016|Asian J.Org.Chem|5|1027|doi:10.1002/ajoc.201600187

CCDC 1045992: Experimental Crystal Structure Determination

Related Article: Michele Bedin, Alavi Karim, Marcus Reitti, Anna-Carin C. Carlsson, Filip Topić, Mario Cetina, Fangfang Pan, Vaclav Havel, Fatima Al-Ameri, Vladimir Sindelar, Kari Rissanen, Jürgen Gräfenstein, Máté Erdélyi|2015|Chemical Science|6|3746|doi:10.1039/C5SC01053E

CCDC 1039550: Experimental Crystal Structure Determination

Related Article: N. Kodiah Beyeh, Altti Ala-Korpi, Fangfang Pan, Hyun Hwa Jo, Eric V. Anslyn, Kari Rissanen|2015|Chem.-Eur.J.|21|9556|doi:10.1002/chem.201406504

CCDC 1519226: Experimental Crystal Structure Determination

Related Article: Sabrina Antonello, Tiziano Dainese, Fangfang Pan, Kari Rissanen, Flavio Maran|2017|J.Am.Chem.Soc.|139|4168|doi:10.1021/jacs.7b00568

CCDC 1036893: Experimental Crystal Structure Determination

Related Article: Markus Albrecht, Hai Yi, Fangfang Pan, Arto Valkonen and Kari Rissanen|2015|Eur.J.Org.Chem.|2015|3235|doi:10.1002/ejoc.201500175

CCDC 1040202: Experimental Crystal Structure Determination

Related Article: Markus Albrecht, Yi Hai, Okan Köksal, Gerhard Raabe, Fangfang Pan, Arto Valkonen and Kari Rissanen|2016|Chem.-Eur.J.|22|6596|doi:10.1002/chem.201600249

CCDC 1574174: Experimental Crystal Structure Determination

Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, John F. Trant, Robin H. A. Ras, Kari Rissanen|2018|Cryst.Growth Des.|18|513|doi:10.1021/acs.cgd.7b01517

CCDC 1556029: Experimental Crystal Structure Determination

Related Article: Lotta Turunen, Fangfang Pan, Ngong Kodiah Beyeh, Mario Cetina, John F. Trant, Robin H. A. Ras, Kari Rissanen|2017|CrystEngComm|19|5223|doi:10.1039/C7CE01118K

CCDC 1497770: Experimental Crystal Structure Determination

Related Article: Stephen S. Nyandoro, Joan J. E. Munissi, Amra Gruhonjic, Sandra Duffy, Fangfang Pan, Rakesh Puttreddy, John P. Holleran, Paul A. Fitzpatrick, Jerry Pelletier, Vicky M. Avery, Kari Rissanen, Máté Erdélyi|2017|J.Nat.Prod.|80|114|doi:10.1021/acs.jnatprod.6b00759

CCDC 1838266: Experimental Crystal Structure Determination

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CCDC 1913150: Experimental Crystal Structure Determination

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CCDC 1995532: Experimental Crystal Structure Determination

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CCDC 1488065: Experimental Crystal Structure Determination

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CCDC 1525501: Experimental Crystal Structure Determination

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CCDC 1424389: Experimental Crystal Structure Determination

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CCDC 1938873: Experimental Crystal Structure Determination

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CCDC 1045991: Experimental Crystal Structure Determination

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CCDC 1417788: Experimental Crystal Structure Determination

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CCDC 1424391: Experimental Crystal Structure Determination

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CCDC 1938868: Experimental Crystal Structure Determination

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CCDC 1022517: Experimental Crystal Structure Determination

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CCDC 1040207: Experimental Crystal Structure Determination

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CCDC 1556032: Experimental Crystal Structure Determination

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CCDC 1498877: Experimental Crystal Structure Determination

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CCDC 1038850: Experimental Crystal Structure Determination

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CCDC 1938872: Experimental Crystal Structure Determination

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CCDC 1938866: Experimental Crystal Structure Determination

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CCDC 1036895: Experimental Crystal Structure Determination

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CCDC 1938869: Experimental Crystal Structure Determination

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CCDC 1045989: Experimental Crystal Structure Determination

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CCDC 1498873: Experimental Crystal Structure Determination

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CCDC 2000611: Experimental Crystal Structure Determination

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CCDC 1498875: Experimental Crystal Structure Determination

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CCDC 1836247: Experimental Crystal Structure Determination

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CCDC 1045994: Experimental Crystal Structure Determination

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CCDC 1836509: Experimental Crystal Structure Determination

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CCDC 1574171: Experimental Crystal Structure Determination

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CCDC 2000613: Experimental Crystal Structure Determination

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CCDC 1407137: Experimental Crystal Structure Determination

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CCDC 1040205: Experimental Crystal Structure Determination

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CCDC 1001536: Experimental Crystal Structure Determination

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CCDC 1417052: Experimental Crystal Structure Determination

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CCDC 1036894: Experimental Crystal Structure Determination

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CCDC 1401638: Experimental Crystal Structure Determination

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CCDC 1427512: Experimental Crystal Structure Determination

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CCDC 1498876: Experimental Crystal Structure Determination

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CCDC 1482002: Experimental Crystal Structure Determination

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CCDC 1894767: Experimental Crystal Structure Determination

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CCDC 1838268: Experimental Crystal Structure Determination

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CCDC 1439770: Experimental Crystal Structure Determination

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CCDC 1452353: Experimental Crystal Structure Determination

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CCDC 1482001: Experimental Crystal Structure Determination

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CCDC 1417791: Experimental Crystal Structure Determination

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CCDC 1045985: Experimental Crystal Structure Determination

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CCDC 1525502: Experimental Crystal Structure Determination

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CCDC 1439769: Experimental Crystal Structure Determination

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CCDC 2000614: Experimental Crystal Structure Determination

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CCDC 1498878: Experimental Crystal Structure Determination

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CCDC 1556028: Experimental Crystal Structure Determination

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CCDC 1497771: Experimental Crystal Structure Determination

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CCDC 1417049: Experimental Crystal Structure Determination

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CCDC 1937082: Experimental Crystal Structure Determination

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CCDC 1894766: Experimental Crystal Structure Determination

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CCDC 1045993: Experimental Crystal Structure Determination

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CCDC 1417050: Experimental Crystal Structure Determination

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CCDC 1045986: Experimental Crystal Structure Determination

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CCDC 1429821: Experimental Crystal Structure Determination

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CCDC 1838267: Experimental Crystal Structure Determination

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CCDC 2051584: Experimental Crystal Structure Determination

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CCDC 1838270: Experimental Crystal Structure Determination

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CCDC 1913148: Experimental Crystal Structure Determination

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CCDC 1424390: Experimental Crystal Structure Determination

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CCDC 1481999: Experimental Crystal Structure Determination

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CCDC 1838269: Experimental Crystal Structure Determination

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CCDC 1556031: Experimental Crystal Structure Determination

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