Creation of Novel Chiral Cryptophanes by a Self-Assembling Method Utilizing a Pyridyl−Pd(II) Interaction

Zhong, Zhenlin; Ikeda, Atsushi; Shinkai, Seiji; Sakamoto, Shigeru; Yamaguchi, Kentaro

doi:10.1021/ol0157205

Cited by 89 publications

(84 citation statements)

References 27 publications

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“…Tripodal derivatives such as those shown in Scheme 1 are chiral. The self-assembly of derivatised CTVs with metal cations is well established, and coordination polymers, [35][36][37] discrete metallocages, [38][39][40][41][42] and mechanically interlocked architectures [43][44][45] are known. However, the chemistry of mixed ligand systems is generally limited to the solution-phase, and we have recently demonstrated how the formation and manipulation of homo-and heteroleptic [Pd 6 L 8 ] 12+ octahedral cages can be controlled with high fidelity.…”

Section: -13mentioning

confidence: 99%

Tuning the coordination chemistry of cyclotriveratrylene ligand pairs through alkyl chain aggregation

Henkelis

Hardie

2014

CrystEngComm

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Section: -13mentioning

confidence: 99%

Tuning the coordination chemistry of cyclotriveratrylene ligand pairs through alkyl chain aggregation

Henkelis

Hardie

2014

CrystEngComm

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“…The self-assembly of derivatised CTVs with metal cations is well established, and coordination polymers, [35][36][37] discrete metallo-cages, [38][39][40][41][42] and mechanically interlocked architectures [43][44][45] are known. However, the chemistry of mixed ligand systems is generally limited to the solution-phase, and we have recently demonstrated how the formation and manipulation of homo-and heteroleptic [Pd 6 L 8 ] 12+ octahedral cages can be controlled with high fidelity.…”

Section: Introductionmentioning

confidence: 99%

Lanthanide coordination polymers with pyridyl-N-oxide or carboxylate functionalised host ligands

2014

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“…ʈ Dynamic interconversion of similar square-planar Pd(II) complexes with pyridyl cycloveratrylenes has been shown by Shinkai et al (37) to occur at room temperature.…”

Section: Resultsmentioning

confidence: 96%

Design and self-assembly of wide and robust coordination cages

Pirondini

Bertolini

Cantadori

et al. 2002

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

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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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Creation of Novel Chiral Cryptophanes by a Self-Assembling Method Utilizing a Pyridyl−Pd(II) Interaction

Cited by 89 publications

References 27 publications

Tuning the coordination chemistry of cyclotriveratrylene ligand pairs through alkyl chain aggregation

Tuning the coordination chemistry of cyclotriveratrylene ligand pairs through alkyl chain aggregation

Lanthanide coordination polymers with pyridyl-N-oxide or carboxylate functionalised host ligands

Design and self-assembly of wide and robust coordination cages

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