Polyaromatic molecular peanuts

Yazaki, Kohei; Akita, Munetaka; Prusty, Soumyakanta; Chand, Dillip Kumar; Kikuchi, Takashi; Sato, Hiroyasu; Yoshizawa, Michito

doi:10.1038/ncomms15914

Cited by 97 publications

(72 citation statements)

References 42 publications

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“…Most recently, Yoshizawa, Chand and co‐workers have developed a “molecular peanut”: a linear double cavity system based on the Yoshizawa group's anthracene panelled single cavity [Pd 2 L 4 ] 4+ cage . The parent single cavity cage system has previously been shown to display rich host–guest chemistry .…”

Section: Linear Extension Of Single Cavity Systemsmentioning

confidence: 99%

Multicavity Metallosupramolecular Architectures

Vasdev

Preston

Crowley

2017

Chemistry An Asian Journal

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Discrete metallosupramolecular systems are often macrocyclic or cage-like architectures with an accessible internal cavity. Guest molecules can reside within these cavities and much of the interest in these systems is derived from these fascinating host-guest interactions. A range of potential applications stem from the ability of these metallosupramolecular architectures to encapsulate guests. These applications include catalysis or acting as molecular reaction flasks, the molecular scavenging of pollutants, storage of reactive species, and drug delivery. Multicavity metallosupramolecular architectures combine the ability of large hollow assemblies to bind multiple guests concurrently with the binding specificity associated with small cages. A variety of different approaches to generating separate compartments within a single metallosupramolecular assembly have emerged. These include interpenetrated cages, cages with polytopic ligands that have a long backbone, and molecules that have two or more clefts. This review examines these approaches, and highlights key contributions to the field.

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Section: Linear Extension Of Single Cavity Systemsmentioning

confidence: 99%

Multicavity Metallosupramolecular Architectures

Vasdev

Preston

Crowley

2017

Chemistry An Asian Journal

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“…We have proven that W-shaped polyaromatic ligands 2 with three pyridine coordination sites ( Figure 1d)q uantitatively assemble into an M 3 L 4 double capsule upon complexation with three Pd II ions. [10] Ther esultant double capsule binds two fullerene molecules in the cavity through the release of the central metal ion. However,b oth the host formation and the guest encapsulation require harsh conditions,s uch as high temperatures (!…”

Section: àmentioning

confidence: 99%

A Peanut‐Shaped Polyaromatic Capsule: Solvent‐Dependent Transformation and Electronic Properties of a Non‐Contacted Fullerene Dimer

et al. 2019

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Synthesis of molecular containers capable of incorporating multiple fullerenes remains challenging. Reported here is that room-temperature mixing of metal ions with W-shaped bispyridine ligands featuring polyaromatic panels results in the quantitative formation of apeanut-shaped M 2 L 4 capsule.T he capsule reversibly converts into two molecules of an ML 2 double tube in response to changes in the solvent. Notably,t he capsule allows the incorporation of two fullerene molecules into the connected two spherical cavities at room temperature.T he close proximity yet noncontact of the encapsulated C 60 molecules,with aseparation of 6.4 ,w as revealed by X-ray crystallographic analysis.T he resultant, unusual fullerene dimer undergoes sequential reduction within the capsule to generate (C 60 C À ) 2 ,C 60 C À ·C 60 2À ,a nd (C 60 2À ) 2 species.Furthermore,temperature-controlled stepwise incorporation of two C 60 molecules into the capsule is demonstrated.Fullerenes themselves provide unique spherical nanostructures as well as advanced redox activities so that their finite and infinite assemblies have been gathering much attention for the development of functional nanocarbon-based devices and materials. [1] Regarding the finite system, there are many reports on covalently linked fullerene assemblies in dumbbell ( Figure 1a) [2] and dendrimer fashions, [3] as well as transitionmetal-directed fullerene assemblies. [4] In contrast, encapsulation of fullerene molecules within molecular containers is another promising method to efficiently prepare discrete fullerene assemblies through noncovalent interactions. [5] Nevertheless,o wing to the large and bulky structures (ca. 1nmi no uter diameter), the synthesis of host compounds capable of selectively binding two or more fullerene guests in the cavity still remains challenging, [6, 7] even though several host structures possess cavities whose sizes are larger than those of ac ouple of fullerenes. [8] Nitschke and co-workers succeeded recently in the preparation of fullerene (C 60 ) n assemblies (n = 2-4, Figure 1b), in which the fullerenes tightly contact each other,u tilizing porphyrin-based coordination cages. [9] However,t he detailed electrochemical characters of fullerene assemblies are still obscure and the redox properties of non-contacted, discrete fullerene assemblies, which are expected to display unique electronic communication, have not been recorded to date.H ere we present as traightforward synthesis of ap eanut-shaped polyaromatic capsule,b yt he self-assembly of metal ions and W-shaped bispyridine ligands (1)w ith embedded polyaromatic panels, and it allows the selective incorporation of two fullerene C 60 molecules with an intermolecular separation of 6.4 (Figure 1c). Then ovel non-contacted fullerene dimer generates (C 60 C À ) 2 ,C 60 C À ·C 60 2À,and (C 60 2À ) 2 species upon electrochemical reduction in the isolated cavity of the capsule.We have proven that W-shaped polyaromatic ligands 2 with three pyridine coordination sites (Figure 1d)q uantitativ...

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“…We call these "aromatic micelles" in contrast with the standard aliphatic micelles. [5][6][7][8][9][10] Oligoarylene Micelles Linearo ligoarylene-basedm icelles Linearr od-coil moleculesc omposed of rigid and flexible blocks form aw ide variety of self-organized, infinite structures in solution and in the solid state. [5][6][7][8][9][10] Oligoarylene Micelles Linearo ligoarylene-basedm icelles Linearr od-coil moleculesc omposed of rigid and flexible blocks form aw ide variety of self-organized, infinite structures in solution and in the solid state.…”

Section: Introductionmentioning

confidence: 99%

Aromatic Micelles as a New Class of Aqueous Molecular Flasks

Kondo

Klosterman

Yoshizawa

2017

Chemistry A European J

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Micelles are a versatile class of molecular assemblies typically composed of aliphatic molecules with hydrophilic groups. Polyaromatic molecules with hydrophilic groups, on the other hand, usually do not assemble into micellar structures in water but rather form columnar, π-stacked architectures. This Minireview article focuses on the recent development of aqueous micellar nanostructures with multiple oligoarylene rods or polyaromatic panels. The new micelles with spherical polyaromatic shells, which we name "aromatic micelles", serve as functional molecular flasks with superior binding abilities for medium to very large molecules in water.

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Polyaromatic molecular peanuts

Cited by 97 publications

References 42 publications

Multicavity Metallosupramolecular Architectures

Multicavity Metallosupramolecular Architectures

A Peanut‐Shaped Polyaromatic Capsule: Solvent‐Dependent Transformation and Electronic Properties of a Non‐Contacted Fullerene Dimer

Aromatic Micelles as a New Class of Aqueous Molecular Flasks

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