Search results for "resorcinarene"
showing 10 items of 166 documents
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…
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
Halogen bonding and host-guest chemistry between
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 …
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.
Nano-sized I12L6 Molecular Capsules Based on the [N⋅⋅⋅I+⋅⋅⋅N] Halogen Bond
2017
Summary Self-assembly of pre-organized subunits with a concave overall shape is an effective strategy for the synthesis of supramolecular capsules. We report the synthesis of a cavitand-based hexameric capsule held together solely by 12 robust [N⋅⋅⋅I + ⋅⋅⋅N] halogen bonds and its characterization in solution and in the gas phase via 1 H NMR spectroscopy, diffusion-ordered nuclear magnetic resonance spectroscopy (DOSY), and electrospray ionization mass spectrometry. The [N⋅⋅⋅I + ⋅⋅⋅N] halogen-bonded hexameric capsule was efficiently synthesized from the isolobal metallosupramolecular Ag + capsule by application of the [N⋅⋅⋅Ag + ⋅⋅⋅N] → [N⋅⋅⋅I + ⋅⋅⋅N] cation-exchange reaction.
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 …
Thermodynamic Interaction Parameters of Tetra-n-undecylcalix[4]resorcinarenes with Selected Solvents Studied by Inverse Gas Chromatography
2004
The basic thermodynamic parameters, characterising intermolecular interactions of tetra-n-undecylcalix[4]resorcinarene and its octaacetate derivative with simple organic solutes, were calculated by using the inverse gas chromatography method. Free energy, enthalpy and entropy of sorption were determined.
A perspective to resorcinarene crowns
2014
In this report, we have summarized different synthesis methods of the resorcinarene crowns, discussed their structural and complexation properties together with the possible application aspects. peerReviewed
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…
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.