Host-guest complexation. 48. Octol building blocks for cavitands and carcerands

Tunstad, Linda M.; Tucker, John; Dalcanale, Enrico; Weiser, Jürgen; Bryant, Judi; Sherman, John C.; Helgeson, Roger C.; Knobler, Carolyn B.; Cram, Donald J.

doi:10.1021/jo00267a015

Cited by 512 publications

(372 citation statements)

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“…The intramolecular hydrogen bonding also explains the stability of the crown conformation [3]. Because of the rigidity of the macrocycle, it is only sparingly soluble in organic solvents and the melting point is high [4]. In addition, resorcarenes are strong H-bond donors because the four hydrogens that are not participating in the intramolecular OH.…”

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confidence: 99%

Alkali metal mediated resorcarene capsules: An ESI-FTICRMS study on gas-phase structure and cation binding of tetraethyl resorcarene and its per-methylated derivative

Mäkinen

Vainiotalo

Rissanen

2002

J. Am. Soc. Mass Spectrom.

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Electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry (ESI-FTICRMS) with additional ab initio calculations were used to examine the alkali metal cation binding selectivity (i.e., molecular recognition) and host properties of tetraethyl resorcarene (1) and its per-methylated derivative (2). The significance of intramolecular hydrogen bonding for the crown conformation was demonstrated. The presence of intramolecular flip-flop hydrogen bonding in 1 was confirmed both with calculations and in ND 3 -exchange experiments. All the alkali metal cations formed host-guest complexes by docking inside the cavity of the host. Complexation with the larger cations, especially Cs ϩ , was favored. All the alkali metal cations also formed dimeric resorcarene capsules with 1. The capsules were directly H-bonded species, with no linking solvent molecules. ND 3 -exchange experiments and molecular modeling revealed the significance of direct intermolecular H-bonding for the crown conformation of 1 and stability of the capsule structure. (J Am Soc Mass Spectrom 2002, 13, 851-861)

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confidence: 99%

Alkali metal mediated resorcarene capsules: An ESI-FTICRMS study on gas-phase structure and cation binding of tetraethyl resorcarene and its per-methylated derivative

Mäkinen

Vainiotalo

Rissanen

2002

J. Am. Soc. Mass Spectrom.

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“…Methylenedioxy-bridgedr esorcin [4]arenes are unique rigid bowl-shaped molecules designed to encapsulate small organic guests [2][3][4]. Resorcincarenes and calixarenes are attractive candidatesf or multifunctional dendritic molecules and several research groups have used their phenols as core molecules for the synthesis of macroscopic structures [5].…”

Section: Discussionmentioning

confidence: 99%

“…Resorcincarenes and calixarenes are attractive candidatesf or multifunctional dendritic molecules and several research groups have used their phenols as core molecules for the synthesis of macroscopic structures [5]. There is no single crystal structure found in the Cambridge Structure Database for methylenedioxy-bridged tetrahydroxy resorcon [4]arene cavitands, only the ethylenedioxy-bridged tetrahydroxy resorcon [4]arene cavitand is present [6]. In that structure, acetone as well as water co-crystallized in the "boat" geometry resorcinarene.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1,21,23,25-tetrapentyl-2,20:3,19-dimetheno- 1H,21H,23H,25H-bis[1,3]dioxocino[5,4-i:5',4'-i']benzo[1,2-d:5,4-d']-bis- [1,3]benzodioxocin-7,11,15,28-tetrol], C56H72O14

Parekh

Pansuriya

Friedrich

et al. 2014

Zeitschrift Für Kristallographie - New Crystal Structures

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“…All solvents were dried over 3-and 4-Å molecular sieves. Resorcinarenes 1a,b were prepared according to the literature (26). Metal precursors were prepared from the corresponding dichlorobis derivatives following established procedures (27)(28)(29).…”

Section: Methodsmentioning

confidence: 99%

Design and self-assembly of wide and robust coordination cages

Pirondini

Bertolini

Cantadori

et al. 2002

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

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The self-assembly of a new class of coordination cages formed from two tetrapyridyl-substituted cavitands connected through four square-planar palladium or platinum complexes is reported. The shape of the internal cavity resembles an ellipsoid with a calculated volume of 840 Å 3 . The four lateral portals have a diameter of about 6 Å, large enough to allow the fast entrance͞ egress of counterions in solution. The platinum cages 3a,e cannot be disassembled using triethylamine as competitive ligand and they are kinetically stable at room temperature, whereas the palladium cages 3b-d, 3f-h are disassembled and kinetically labile under the same conditions. The different solubility properties of the cage components have allowed the extension of this selfassembly protocol to the liquid-liquid interface. cavitands M etal-directed self-assembly has been widely used to construct three-dimensional structures presenting internal cavities of molecular dimensions, capable of trapping ions and neutral molecules (1, 2). The ability of such container molecules to confine (3) and stabilize (4) their guests makes them particularly attractive for many potential applications ranging from catalysis (5, 6) to nanotechnology (for self-assembly in nanotechnology, see ref. 7; ref. 8). Specifically, surface-controlled self-assembly is rapidly emerging as a valuable tool for the generation of complex structures directly on solid supports (9-11). Unlike the covalent approach used for carcerands synthesis (12), the thermodynamic control of the process conveys interesting features, among which reversibility (13), selection (14), and self-repairing properties are the most interesting.Cavitand-based coordination cages are receiving increasing attention because of the versatility of cavitand platforms in terms of preorganization and synthetic modularity (15)(16)(17)(18)(19)(20). Strong metal-ligand interactions are necessary to operate cage selfassembly (CSA) in a wide range of solvents, to extend further these self-assembly protocols to solid-liquid and liquid-liquid interfaces.For this purpose we designed and synthesized new cavitands bearing pyridines (for references on cages derived from multidentate pyridine ligands, see ref. 21; refs. 22 and 23) instead of nitriles (24) at the upper rim as ligands for the coordination to the metal centers. CSA requires a cavitand with four pyridines preorganized in a diverging spatial orientation, pointing outward (o) the cavity, being designated the oooo isomer (for in͞out isomerism in cavitands, see ref. 25). Materials and MethodsGeneral. All commercial reagents were ACS reagent grade and used as received. All solvents were dried over 3-and 4-Å molecular sieves. Resorcinarenes 1a,b were prepared according to the literature (26). Metal precursors were prepared from the corresponding dichlorobis derivatives following established procedures (27-29). 1 H NMR were recorded on Bruker (Billerica, MA) AC300 (300 MHz) and AMX400 (400 MHz) spectrometers and all chemical shifts (␦) were reported in parts per milli...

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Host-guest complexation. 48. Octol building blocks for cavitands and carcerands

Cited by 512 publications

References 0 publications

Alkali metal mediated resorcarene capsules: An ESI-FTICRMS study on gas-phase structure and cation binding of tetraethyl resorcarene and its per-methylated derivative

Alkali metal mediated resorcarene capsules: An ESI-FTICRMS study on gas-phase structure and cation binding of tetraethyl resorcarene and its per-methylated derivative

Crystal structure of 1,21,23,25-tetrapentyl-2,20:3,19-dimetheno- 1H,21H,23H,25H-bis[1,3]dioxocino[5,4-i:5',4'-i']benzo[1,2-d:5,4-d']-bis- [1,3]benzodioxocin-7,11,15,28-tetrol], C56H72O14

Design and self-assembly of wide and robust coordination cages

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