Five-fold symmetric penta-substituted corannulene with gelation properties and a liquid-crystalline phase

Mattarella, Martin; Haberl, Johannes M.; Ruokolainen, Janne; Landau, Ehud M.; Mezzenga, Raffaele; Siegel, Jay S.

doi:10.1039/c3cc41476k

Cited by 27 publications

(29 citation statements)

References 24 publications

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“…These interesting compounds provide potential applications in bioconjugated chemistry [95] and organic materials, which display liquid-crystalline behavior and organogelation properties [96].…”

Section: T-bu T-bu T-bu T-bu T-bumentioning

confidence: 99%

Synthesis, Structures, and Physical Properties of Aromatic Molecular-Bowl Hydrocarbons

Siegel

2014

Topics in Current Chemistry

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This chapter summarizes the synthesis, physical properties, structure, and crystal packing of buckybowls. Buckybowls exemplify an intermediate class of polynuclear aromatic compounds between the closed-shell fullerenes and the flat extended arrays of graphene. These warped sheets can be seen as fragments of fullerenes or the end cap of single-walled carbon nanotubes; and, their curvature endows them with physical properties distinct from flat polynuclear hydrocarbons, which opens up unique possibilities for molecular bowls in various organic materials applications.

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Section: T-bu T-bu T-bu T-bu T-bumentioning

confidence: 99%

Synthesis, Structures, and Physical Properties of Aromatic Molecular-Bowl Hydrocarbons

Siegel

2014

Topics in Current Chemistry

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“…Bowlic (or bowl-like) supramolecules including corannulenes, [1][2][3] sub-phthalocyanines, [4] calix[n]arenes [5][6][7][8] are 3D structures with cavities, which exhibit unique bowlic liquid crystalline mesophases, [9][10][11][12][13] making them promising candidates for ultrahigh-density memory device materials. The calix[n]arenes, cyclic arene oligomers with n repeating units, in particular present the ability to complex with various ions and neutral guests, [13][14][15][16][17] opening up opportunities for developing responsive and switchable ferroelectric devices.…”

Section: Introductionmentioning

confidence: 99%

Self‐Assembly of Bowlic Supramolecules on Graphene Imaged at the Individual Molecular Level using Heavy Atom Tagging

Kengmana

Lee

et al. 2020

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The self‐assembly of bowlic supramolecules on graphene surface is studied with single molecular sensitivity. This is achieved by incorporating a heavy metal tag in the form of a single W atom into the tip of the molecular structure, which enables the direct imaging of molecular distribution using annular dark‐field scanning transmission electron microscopy (ADF‐STEM) along with graphene as an electron transparent support. The bowlic molecules have nonplanar geometry, and their orientations with respect to their graphene substrate and with each other result in various packing configurations. Statistical data on intermolecular distances is obtained from numerous measurements of the bright contrast from the single metal atom tags. The analysis shows that the bowlic molecules lie sideways on the graphene surface with favorable head‐to‐tail stacking, rather than sitting vertically with the bowl facing toward the graphene surface. In thicker film regions, nanoscale lamellar fringes are observed, demonstrating that large‐scale aligned packing extends into 3D. Image simulations and various molecular packing schemes are discussed to help interpret the ADF‐STEM images and the possible range of molecular interactions occurring. These results aid the understanding of nonplanar supramolecular assemblies on van der Waals surfaces for potential applications in molecular recognition by porous films.

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“…One involves the substitution of the corannulene nucleus with long alkyl chains and the other is based upon hydrogen‐bonding interactions between adjacent assembly precursors , . Siegel and co‐workers, on the other hand, have shown that lipid modification or oligosaccharide substitution of the corannulene scaffold can render the structures prone to aggregation into larger supramolecular assemblies , . Finally, Maeda and co‐workers have also substituted the corannulene unit with multiple alkyl chains to facilitate aggregation .…”

Section: Introductionmentioning

confidence: 99%

Thermoresponsive Corannulene

Mahadevegowda

Stuparu

2017

Eur J Org Chem

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We demonstrate herein that corannulene, a bowl‐shaped polycyclic aromatic hydrocarbon, can assemble into larger supramolecular structures in water through a change in the solution temperature. This property is invoked through a simple five‐fold symmetric substitution of the corannulene nucleus with triethylene glycol units. Interestingly, an increase in the solution temperature, which triggers the assembly process, also enhances the fluorescence emission properties of the assembled materials. Although the emission remains very weak in solution, bright green luminescence can be observed in the fibrilar form. This unexpected and interesting behavior indicates that the corannulene nucleus presents a new motif for the design of aggregation‐induced emission (AIE) based luminogens. To the best of our knowledge, this is the first report of a thermoresponsive nonplanar polycyclic hydrocarbon derivative that can respond to a thermal trigger and assemble into larger emissive structures.

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Five-fold symmetric penta-substituted corannulene with gelation properties and a liquid-crystalline phase

Abstract: Five-fold symmetric substituted corannulene derivatives that display liquid-crystalline behavior and organogelation properties were prepared by coupling of N-azidoethyl long-chain fatty acid amides to sym-pentabutynyl corannulenes via dipolar cycloaddition chemistry.

Cited by 27 publications

References 24 publications

Synthesis, Structures, and Physical Properties of Aromatic Molecular-Bowl Hydrocarbons

Synthesis, Structures, and Physical Properties of Aromatic Molecular-Bowl Hydrocarbons

Self‐Assembly of Bowlic Supramolecules on Graphene Imaged at the Individual Molecular Level using Heavy Atom Tagging

Thermoresponsive Corannulene

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