Host–Guest Interactions of Sodiumsulfonatomethyleneresorcinarene and Quaternary Ammonium Halides: An Experimental–Computational Analysis of the Guest…

2020

The molecular recognition of nine quaternary alkyl- and aryl-ammonium halides (Bn) by two different receptors, Calkyl-tetrasodiumsulfonatomethyleneresorcinarene (An), were studied in solution using...

Tetraiodoethynyl resorcinarene cavitands as multivalent halogen bond donors

2014

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.

Piperazine bridged resorcinarene cages.

2010

The one-pot Mannich condensation of resorcinarenes with piperazine and an excess of formaldehyde under high dilution conditions results in a helical cage, namely, a covalently linked dimer of two resorcinarenes connected via four piperazine bridges in yields ranging from 20 to 40%. The compounds were analyzed by NMR spectroscopy, ESI mass spectrometry, and single crystal X-ray diffraction. The helical cages can encapsulate small guest molecules by adapting the cavity volume by changing the helical pitch according to the guest size.

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

2016

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…

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

2015

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…

Inclusion complexes of Cethyl-2-methylresorcinarene and pyridine N-oxides: breaking the C–I⋯−O–N+ halogen bond by host–guest complexation

2016

C ethyl-2-Methylresorcinarene forms host–guest complexes with aromatic N-oxides through multiple intra- and intermolecular hydrogen bonds and C–H⋯π interactions. The host shows conformational flexibility to accommodate 3-methylpyridine N-oxide, while retaining a crown conformation for 2-methyl- and 4-methoxypyridine N-oxides highlighting the substituent effect of the guest. N-Methylmorpholine N-oxide, a 6-membered ring aliphatic N-oxide with a methyl at the N-oxide nitrogen, is bound by the equatorial −N–CH3 group located deep in the cavity. 2-Iodopyridine N-oxide is the only guest that manifests intermolecular N–O⋯I–C halogen bond interactions, which are broken down by the host resulting i…

Sharing the salt bowl: counterion identity drives N-alkyl resorcinarene affinity for pyrophosphate in water

2021

N-Alkyl ammonium resorcinarene chloride receptors, NARX4, have been shown to act as high-sensitivity detectors of pyrophosphate (PPi), a biomarker of disease, in aqueous media through the chloride-to-PPi exchange [NAR(Cl)4 to NARPPi]. The nature of the anion of the macrocyclic NARX4 (X = Cl−, Br−, triflate OTf−) receptor greatly influences the PPi-affinity in aqueous media. The binding affinity for [NAR (Cl)4] is 3.61 × 105 M−1, while the NAR (Br)4 and NAR (OTf)4 show stronger binding of 5.30 × 105 M−1, and 6.10 × 105 M−1, respectively. The effects of upper rim ammonium cation, –N+H2R substituents (R = 3-hydroxypropyl, cyclohexyl, benzyl, or napththalen-1-ylmethyl), of the macrocyclic resor…

Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies

2018

Host–guest complexes of C-hexyl-2-bromoresorcinarene (BrC6) with twelve potential aromatic N-oxide guests were studied using single crystal X-ray diffraction analysis and 1H NMR spectroscopy. In the solid state, of the nine obtained X-ray crystal structures, eight were consistent with the formation of BrC6-N-oxide endo complexes. The lone exception was from the association between 4-phenylpyridine N-oxide and BrC6, in that case the host forms a self-inclusion complex. BrC6, as opposed to more rigid previously studied C-ethyl-2-bromoresorcinarene and C-propyl-2-bromoresorcinarene, undergoes remarkable cavity conformational changes to host different N-oxide guests through C–H···π(host) intera…

Fliegende Kapseln: massenspektrometrische Detektion von Pyrogallaren- und Resorcinaren-Hexameren

2006

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

2016

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…

A Halogen-Bonded Dimeric Resorcinarene Capsule.

2015

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.

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

2017

Conformational changes in Cmethyl-resorcinarene pyridine N -oxide inclusion complexes in the solid state

2016

Aromatic N-oxides interact with Cmethyl-resorcinarene resulting in marked changes in the conformation of the host resorcinarene. In the solid state, 2- and 3-methylpyridine N-oxides form pseudo-capsular 2 : 2 endo host-guest complexes with Cmethyl-resorcinarene stabilized by C-H⋯π interactions. The Cmethyl-resorcinarene·2-methylpyridine N-oxide complex has a C4v crown conformation, while the Cmethyl-resorcinarene·3-methylpyridine N-oxide complex has a slightly open C2v boat conformation. On the contrary, other para-substituted and benzo-fused pyridine N-oxides form only exo complexes with Cmethyl-resorcinarene. In the exo complexes, the asymmetry of the guest, conformational flexibility and…

High-affinity and selective detection of pyrophosphate in water by a resorcinarene salt receptor

2017

N-Alkyl ammonium resorcinarenes selectively bind pyrophosphate in pure water with an exceptionally high binding constant of up to 1.60 × 107 M–1, three orders of magnitude higher than ATP.

Host-guest complexes of C-propyl-2-bromoresorcinarene with aromatic N-oxides*

2017

The host-guest complexes of C-propyl-2-bromoresorcinarene with pyridine N-oxide, 3-methylpyridine N-oxide, quinoline N-oxide and isoquinoline N-oxide are studied using single crystal X-ray crystallography and 1H NMR spectroscopy. The C-propyl-2-bromoresorcinarene forms endo-complexes with the aromatic N-oxides in the solid-state when crystallised from either methanol or acetone. In solution, the endo-complexes were observed only in methanol-d4. In DMSO the solvent itself is a good guest, and crystallisation provides only solvate endo-complexes. The C-propyl-2-bromoresorcinarene shows remarkable flexibility when crystallised from either methanol or acetone, and packs into one-dimensional sel…

Host-Guest Complexes of C-Ethyl-2-methylresorcinarene and Aromatic N,N′-Dioxides

2017

The C‐ethyl‐2‐methylresorcinarene (1) forms 1:1 in‐cavity complexes with aromatic N,N′‐dioxides, only if each of the aromatic rings has an N−O group. The structurally different C‐shaped 2,2′‐bipyridine N,N′‐dioxide (2,2′‐BiPyNO) and the linear rod‐shaped 4,4′‐bipyridine N,N′‐dioxide (4,4′‐BiPyNO) both form 1:1 in‐cavity complexes with the host resorcinarene in C4v crown and C2v conformations, respectively. In the solid state, the host–guest interactions between the 1,3‐bis(4‐pyridyl)propane N,N′‐dioxide (BiPyPNO) and the host 1 stabilize the unfavorable anti‐gauche conformation. Contrary to the N,N′‐dioxide guests, the mono‐N‐oxide guest, 4‐phenylpyridine N‐oxide (4PhPyNO), does not form an…

[N⋅⋅⋅I+⋅⋅⋅N] Halogen-Bonded Dimeric Capsules from Tetrakis(3-pyridyl)ethylene Cavitands

2016

Two [N⋅⋅⋅I+⋅⋅⋅N] halogen-bonded dimeric capsules using tetrakis(3-pyridyl)ethylene cavitands with different lower rim alkyl chains are synthesized and analyzed in solution and the gas phase. These first examples of symmetrical dimeric capsules making use of the iodonium ion (I+) as the main connecting module are characterized by 1H NMR spectroscopy, diffusion ordered NMR spectroscopy (DOSY), electrospray ionization mass spectrometry (ESI-MS), and ion mobility-mass spectrometry (TW-IMS) experiments. The synthesis and effective halogen-bonded dimerization proceeds through analogous dimeric capsules with [N⋅⋅⋅Ag+⋅⋅⋅N] binding motifs as the intermediates as evidenced by the X-ray structures of …

Thermodynamically driven self-assembly of pyridinearene to hexameric capsules

2019

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 …

Flying Capsules: Mass Spectrometric Detection of Pyrogallarene and Resorcinarene Hexamers

2006

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

2017

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…

Self-Complementary Dimers of Oxalamide-Functionalized Resorcinarene Tetrabenzoxazines

2018

Self‐complementarity is a useful concept in supramolecular chemistry, molecular biology and polymeric systems. Two resorcinarene tetrabenzoxazines decorated with four oxalamide groups were synthesized and characterized. The oxalamide groups possessed self‐complementary hydrogen bonding sites between the carbonyls and amide groups. The self‐complementary nature of the oxalamide groups resulted in self‐included dimeric assemblies. The hydrogen bonding interactions within the tetrabenzoxazines gave rise to the formation of dimers, which were confirmed by single‐crystal X‐ray diffractions analysis and supported by NMR spectroscopy and mass spectrometry. The self‐included dimers were connected b…

Halogen-bonded solvates of tetrahaloethynyl cavitands

2017

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.

The “nitrogen effect” : Complexation with macrocycles potentiates fused heterocycles to form halogen bonds in competitive solvents

2023

Weak intermolecular forces are typically very difficult to observe in highly competitive polar protic solvents as they are overwhelmed by the quantity of competing solvent. This is even more challenging for three-component ternary assemblies of pure organic compounds. In this work, we overcome these complications by leveraging the binding of fused aromatic N-heterocycles in an open resorcinarene cavity to template the formation of a three-component halogen-bonded ternary assembly in a protic polar solvent system. peerReviewed

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

2018

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…

Encapsulation of xenon by bridged resorcinarene cages with high 129Xe NMR chemical shift and efficient exchange dynamics

2023

Functionalized cages encapsulating xenon atoms enable highly sensitive, background-free molecular imaging through a technique known as HyperCEST 129Xe MRI. Here, we introduce a class of potential biosensor cage structures based on two resorcinarene macrocycles bridged either by aliphatic carbon chains or piperazines. First-principles-based modeling predicts a high chemical shift (about 345 ppm) outside the typical experimental observation window for 129Xe encapsulated by the aliphatically bridged cage and two 129Xe resonances for the piperazine-bridged cages corresponding to single and double loading. Based on the computational predictions as well as 129Xe chemical exchange saturation trans…

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

2016

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

Recent Advances in Halogen Bonded Assemblies with Resorcin[4]arenes

2020

Resorcinarenes are cavity-containing compounds when in the crown conformation, from the calixarene family of concave compounds. These easy to synthesize macrocycles can be decorated at the upper rim through the eight hydroxyl groups and/or the 2-position of the aromatic ring. They are good synthons in supramolecular chemistry leading to appealing assemblies such as open-inclusion complexes, capsules and tubes through multiple weak interactions with various guests. Halogen bonding (XB) is a highly directional non-covalent interaction by an electron-deficient halogen atom as a donor that interacts with a Lewis base, the XB acceptor. This tutorial review provides an overview of recent advances…

N-Alkyl ammonium resorcinarene polyiodides

2016

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.

N-Alkyl Ammonium Resorcinarene Salts: A Versatile Family of Calixarene-Related Host Molecules

2016

This chapter presents a review of the recent advances in the chemistry of N-alkylammonium resorcinarenes salt receptors. The Mannich condensation between amines (primary and secondary) and resorcinarenes result in resorcinarene tetrabenzoxazines and tetra-azoxazines. Only 2 isomers out of 16 potential isomers are formed. The resorcinarene tetrabenzoxazines possess deeper cavities than the parent resorcinarenes which are suitable for binding neutral and cationic guests. In the presence of mineral acids, the six-membered oxazine ring in the resorcinarene tetrabenzoxazines is opened, resulting in N-alkylammonium resorcinarene salts (NARSs). The NARSs possess four spatially-fixed anions within …

Host-guest complexes of C-propyl-2-bromoresorcinarene with aromatic N-oxides*

2018

The host-guest complexes of C-propyl-2-bromoresorcinarene with pyridine N-oxide, 3-methylpyridine N-oxide, quinoline N-oxide and isoquinoline N-oxide are studied using single crystal X-ray crystallography and 1H NMR spectroscopy. The C-propyl-2-bromoresorcinarene forms endo-complexes with the aromatic N-oxides in the solid-state when crystallised from either methanol or acetone. In solution, the endo-complexes were observed only in methanol-d4. In DMSO the solvent itself is a good guest, and crystallisation provides only solvate endo-complexes. The C-propyl-2-bromoresorcinarene shows remarkable flexibility when crystallised from either methanol or acetone, and packs into one-dimensional sel…

Endo-/exo- and halogen-bonded complexes of conformationally rigid C-ethyl-2-bromoresorcinarene and aromatic N-oxides

2017

The host-guest complexes of conformationally rigid C-ethyl-2-bromoresorcinarene with aromatic N-oxides were studied using single crystal X-ray crystallography. Unlike that of the conformationally more flexible C-ethyl-2-methylresorcinarene, the C-ethyl-2-bromoresorcinarene cavity forms endo-complexes only with the small pyridine-N-oxides, such as pyridine N-oxide, 2-methyl-, 3-methyl- and 4-methylpyrdine N-oxide, and quinoline N-oxide. The larger 2,4,6-trimethylpyridine, 4-phenylpyridine and isoquinoline N-oxide, and 4,4-bipyridine N,N′-dioxide and 1,3-bis(4-pyridyl)propane N,N′-dioxide do not fit into the host cavity. Instead endo-acetone complexes are formed. Remarkably, differing from th…

Encapsulation of tetramethylphosphonium cations

2009

International audience; The weak interactions and capsule formation of tetramethylphosphonium (TMP) cation with resorcinarenes 1 and 2 and the corresponding pyrogallarenes 3 and 4 were studied in the solid state by single crystal X-ray diffraction, in solution by NMR and in the gas phase by mass spectrometry. In methanol-D4, the NMR titration studies reveal that the association constants for the 1:1 complexes of TMP@3 and TMP@4 are much higher (TMP@4:390±37 M-1) than for the corresponding TMP@1 and TMP@2 (TMP@2:130±10 M-1) complexes. In the gas phase both monomeric 1:1 TMP@1-TMP@4 complexes as well as the dimeric 1:2 capsule complexes, TMP@12-TMP@42 were observed. The 1:1:2 molar mixtures o…

Aromatic N-oxide templates open inclusion and dimeric capsular assemblies with methylresorcinarene

2015

C2-2-methylresorcinarene forms host–guest complexes with pyridine N-oxide and quinoline N-oxide. In solution the NMR studies support the 1 : 1 host–guest complexes while in the solid state, the single crystal X-ray diffraction studies reveal dimeric capsule-like assemblies with 2 : 3 and 2 : 2 host–guest stoichiometry.

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

2020

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…

Methylresorcinarene: a reaction vessel to control the coordination geometry of copper(II) in pyridine N-oxide copper(II) complexes

2015

Pyridine and 2-picolinic acid N-oxides form 2 : 2 and 2 : 1 ligand : metal (L : M) discrete L2M2 and polymeric complexes with CuCl2 and Cu(NO3)2, respectively, with copper(ii) salts. The N-oxides also form 1 : 1 host-guest complexes with methylresorcinarene. In combination, the three components form a unique 2 : 2 : 1 host-ligand-metal complex. The methylresorcinarene acts as a reaction vessel/protecting group to control the coordination of copper(ii) from cis-see-saw to trans-square planar, and from octahedral to square planar coordination geometry. These processes were studied in solution and in the solid state via(1)H NMR spectroscopy and single crystal X-ray diffraction.

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

2019

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 …

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

2017

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.

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

2015

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

2016

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…

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

2017

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…

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

2017

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

Inclusion complexes of Cethyl-2-methylresorcinarene and pyridine N-oxides: breaking the C–I⋯−O–N+ halogen bond by host–guest complexation

2016

C ethyl-2-Methylresorcinarene forms host–guest complexes with aromatic N-oxides through multiple intra- and intermolecular hydrogen bonds and C–H⋯π interactions. The host shows conformational flexibility to accommodate 3-methylpyridine N-oxide, while retaining a crown conformation for 2-methyl- and 4-methoxypyridine N-oxides highlighting the substituent effect of the guest. N-Methylmorpholine N-oxide, a 6-membered ring aliphatic N-oxide with a methyl at the N-oxide nitrogen, is bound by the equatorial −N–CH3 group located deep in the cavity. 2-Iodopyridine N-oxide is the only guest that manifests intermolecular N–O⋯I–C halogen bond interactions, which are broken down by the host resulting i…

Host-Guest Interactions of Sodiumsulfonatomethyleneresorcinarene and Quaternary Ammonium Halides : An Experimental-Computational Analysis of the Gues…

2020

The molecular recognition of nine quaternary alkyl- and aryl-ammonium halides (Bn) by two different receptors, Calkyl-tetrasodiumsulfonatomethyleneresorcinarene (An), were studied in solution using 1H NMR spectroscopy. Substitution of methylenesulfonate groups at 2-positions of resorcinol units resulted in an increase of cavity depth by ∼2.80 Å and a narrow cavity aperture compared to Calkyl-2-H-resorcinarenes. The effect of alkyl chain lengths on the endo-complexation, that is the ability to incorporate other than N-methyl chains inside the cavities, were investigated using ammonium cations of the type ⁺NH2(R1)(R2), (R1 = Me, Et, Bu, R2 = Bu, Ph, Bz ). The C−H⋯ interactions between guests …

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

2015

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

2020

C-Ethyl-2-Methylresorcinarene (A), pyridine (B), and a set of ten 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 non-covalent interactions organizes the complexes even in a highly hydrogen-bond competing methanol solution as explored by both experimental and computational methods. The interactions be-tween A·B and Cn are dependent on the pKa values of carboxylic acids. The weak interactions between A and C further reinforce the interactions b…

Endo-/Exo- and Halogen Bonded Complexes of Conformationally Rigid Cethyl-2-bromoresorcinarene and aromatic N-oxides

2017

The host–guest complexes of conformationally rigid C-ethyl-2-bromoresorcinarene with aromatic N-oxides were studied using single crystal X-ray crystallography. Unlike that of the conformationally more flexible C-ethyl-2-methylresorcinarene, the C-ethyl-2-bromoresorcinarene cavity forms endo-complexes only with the small pyridine-N-oxides, such as pyridine N-oxide, 2-methyl-, 3-methyl- and 4-methylpyrdine N-oxide, and quinoline N-oxide. The larger 2,4,6-trimethylpyridine, 4-phenylpyridine and isoquinoline N-oxide, and 4,4-bipyridine N,N′-dioxide and 1,3-bis(4-pyridyl)propane N,N′-dioxide do not fit into the host cavity. Instead endo-acetone complexes are formed. Remarkably, differing from th…

CCDC 1051388: Experimental Crystal Structure Determination

2017

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

CCDC 1450585: Experimental Crystal Structure Determination

2016

Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Kari Rissanen|2016|CrystEngComm|18|4971|doi:10.1039/C6CE00240D

CCDC 1407239: Experimental Crystal Structure Determination

2016

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CCDC 1481997: Experimental Crystal Structure Determination

2016

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CCDC 1473236: Experimental Crystal Structure Determination

2017

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CCDC 1551407: Experimental Crystal Structure Determination

2017

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CCDC 1450588: Experimental Crystal Structure Determination

2016

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CCDC 1543476: Experimental Crystal Structure Determination

2017

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CCDC 1051458: Experimental Crystal Structure Determination

2015

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CCDC 1938867: Experimental Crystal Structure Determination

2020

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CCDC 1054267: Experimental Crystal Structure Determination

2015

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CCDC 1551402: Experimental Crystal Structure Determination

2017

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CCDC 1966175: Experimental Crystal Structure Determination

2020

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CCDC 1525503: Experimental Crystal Structure Determination

2017

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CCDC 2231744: Experimental Crystal Structure Determination

2023

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CCDC 1577820: Experimental Crystal Structure Determination

2018

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CCDC 1556027: Experimental Crystal Structure Determination

2017

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CCDC 1407242: Experimental Crystal Structure Determination

2016

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CCDC 1577819: Experimental Crystal Structure Determination

2018

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CCDC 1583123: Experimental Crystal Structure Determination

2018

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CCDC 1488064: Experimental Crystal Structure Determination

2016

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CCDC 1488067: Experimental Crystal Structure Determination

2016

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CCDC 1054272: Experimental Crystal Structure Determination

2015

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CCDC 1938870: Experimental Crystal Structure Determination

2020

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CCDC 1837609: Experimental Crystal Structure Determination

2020

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CCDC 1938871: Experimental Crystal Structure Determination

2020

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CCDC 1551412: Experimental Crystal Structure Determination

2017

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CCDC 1583131: Experimental Crystal Structure Determination

2018

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CCDC 1452468: Experimental Crystal Structure Determination

2016

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CCDC 1966174: Experimental Crystal Structure Determination

2020

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CCDC 1498390: Experimental Crystal Structure Determination

2016

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CCDC 1577818: Experimental Crystal Structure Determination

2018

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CCDC 1556030: Experimental Crystal Structure Determination

2017

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CCDC 1837606: Experimental Crystal Structure Determination

2019

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CCDC 1439768: Experimental Crystal Structure Determination

2016

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CCDC 1481998: Experimental Crystal Structure Determination

2016

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CCDC 1583125: Experimental Crystal Structure Determination

2018

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CCDC 1051459: Experimental Crystal Structure Determination

2015

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CCDC 1556033: Experimental Crystal Structure Determination

2017

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CCDC 1407240: Experimental Crystal Structure Determination

2016

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CCDC 1417020: Experimental Crystal Structure Determination

2015

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CCDC 1054270: Experimental Crystal Structure Determination

2015

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CCDC 1837611: Experimental Crystal Structure Determination

2020

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CCDC 1583130: Experimental Crystal Structure Determination

2018

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CCDC 1551404: Experimental Crystal Structure Determination

2017

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CCDC 1837608: Experimental Crystal Structure Determination

2020

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CCDC 1583128: Experimental Crystal Structure Determination

2018

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CCDC 1439767: Experimental Crystal Structure Determination

2016

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CCDC 1837605: Experimental Crystal Structure Determination

2019

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CCDC 1417051: Experimental Crystal Structure Determination

2015

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CCDC 1417021: Experimental Crystal Structure Determination

2015

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CCDC 1473237: Experimental Crystal Structure Determination

2017

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CCDC 1407241: Experimental Crystal Structure Determination

2016

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CCDC 1574172: Experimental Crystal Structure Determination

2017

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CCDC 1481996: Experimental Crystal Structure Determination

2016

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CCDC 1488066: Experimental Crystal Structure Determination

2016

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CCDC 1452743: Experimental Crystal Structure Determination

2016

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CCDC 1551411: Experimental Crystal Structure Determination

2017

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CCDC 1574174: Experimental Crystal Structure Determination

2017

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CCDC 1556029: Experimental Crystal Structure Determination

2017

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CCDC 1551410: Experimental Crystal Structure Determination

2017

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CCDC 1488065: Experimental Crystal Structure Determination

2016

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CCDC 1583127: Experimental Crystal Structure Determination

2018

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CCDC 1525501: Experimental Crystal Structure Determination

2017

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CCDC 1938873: Experimental Crystal Structure Determination

2020

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CCDC 1551408: Experimental Crystal Structure Determination

2017

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CCDC 1938868: Experimental Crystal Structure Determination

2020

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CCDC 1556032: Experimental Crystal Structure Determination

2017

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CCDC 1450587: Experimental Crystal Structure Determination

2016

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CCDC 1938872: Experimental Crystal Structure Determination

2020

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CCDC 1938866: Experimental Crystal Structure Determination

2020

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CCDC 1551406: Experimental Crystal Structure Determination

2017

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CCDC 1054269: Experimental Crystal Structure Determination

2015

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CCDC 1450583: Experimental Crystal Structure Determination

2016

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CCDC 1938869: Experimental Crystal Structure Determination

2020

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CCDC 1450586: Experimental Crystal Structure Determination

2016

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CCDC 1837612: Experimental Crystal Structure Determination

2020

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CCDC 1450582: Experimental Crystal Structure Determination

2016

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CCDC 1551403: Experimental Crystal Structure Determination

2017

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CCDC 1574171: Experimental Crystal Structure Determination

2017

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CCDC 1837607: Experimental Crystal Structure Determination

2019

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CCDC 1529901: Experimental Crystal Structure Determination

2021

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CCDC 1417052: Experimental Crystal Structure Determination

2015

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CCDC 1529902: Experimental Crystal Structure Determination

2021

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CCDC 1894767: Experimental Crystal Structure Determination

2019

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CCDC 1054268: Experimental Crystal Structure Determination

2015

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CCDC 1439770: Experimental Crystal Structure Determination

2016

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

CCDC 1583124: Experimental Crystal Structure Determination

2018

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CCDC 1899745: Experimental Crystal Structure Determination

2019

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CCDC 1407237: Experimental Crystal Structure Determination

2016

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CCDC 1966171: Experimental Crystal Structure Determination

2020

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CCDC 1525502: Experimental Crystal Structure Determination

2017

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CCDC 1439769: Experimental Crystal Structure Determination

2016

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CCDC 1450584: Experimental Crystal Structure Determination

2016

Related Article: Rakesh Puttreddy, Ngong Kodiah Beyeh, Kari Rissanen|2016|CrystEngComm|18|4971|doi:10.1039/C6CE00240D

CCDC 1556028: Experimental Crystal Structure Determination

2017

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CCDC 1551405: Experimental Crystal Structure Determination

2017

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CCDC 1837604: Experimental Crystal Structure Determination

2019

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CCDC 1583126: Experimental Crystal Structure Determination

2018

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CCDC 1966173: Experimental Crystal Structure Determination

2020

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CCDC 1417049: Experimental Crystal Structure Determination

2015

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CCDC 1054271: Experimental Crystal Structure Determination

2015

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CCDC 1583122: Experimental Crystal Structure Determination

2018

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CCDC 1529904: Experimental Crystal Structure Determination

2021

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CCDC 1894766: Experimental Crystal Structure Determination

2019

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CCDC 1417050: Experimental Crystal Structure Determination

2015

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CCDC 1407238: Experimental Crystal Structure Determination

2016

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CCDC 1583129: Experimental Crystal Structure Determination

2018

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CCDC 1966172: Experimental Crystal Structure Determination

2020

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CCDC 1551401: Experimental Crystal Structure Determination

2017

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CCDC 1481999: Experimental Crystal Structure Determination

2016

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CCDC 1556031: Experimental Crystal Structure Determination

2017

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CCDC 1551409: Experimental Crystal Structure Determination

2017

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CCDC 1837610: Experimental Crystal Structure Determination

2020

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CCDC 1529903: Experimental Crystal Structure Determination

2021

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