Shape‐Persistent Macrocycles: From Molecules to Materials

Höger, Sigurd

doi:10.1002/chem.200305496

Cited by 299 publications

(105 citation statements)

References 76 publications

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“…Shape-persistent macrocycles with porous cavities, capable of forming ordered columnar structures, have been synthesized both by a geometry-driven and a templated approach. [51][52][53][54] However, few of these macrocycles possess an extended p-conjugation. [55,56] In order to check a new concept of extended conjugation length, para-coupled phenylene units were introduced instead of meta-coupled units.…”

Section: P-conjugated Polyphenylene Macrocyclesmentioning

confidence: 99%

Polyphenylene‐Based Materials: Control of the Electronic Function by Molecular and Supramolecular Complexity

2009

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Organic electronics is one of the hottest and most exciting research topics today. However, its performance still lags behind that of inorganic‐based electronics. This Progress Report demonstrates that by controlling the complexity of organic molecules at the molecular and at the supramolecular level as well as by choosing suitable processing techniques, the desired function for applications in electronics can be achieved. Our main focus is on polyphenylene‐based nanomaterials, versatile organic molecules that allow access to novel intricate materials. We emphasize the molecular complexity as well as the supramolecular organization and the interfacing of novel organic materials as key guidelines.

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Section: P-conjugated Polyphenylene Macrocyclesmentioning

confidence: 99%

Polyphenylene‐Based Materials: Control of the Electronic Function by Molecular and Supramolecular Complexity

2009

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“…[30,31,39,48] Appropriate peripheral decoration also enhances the self-assembly properties [33,34,49] of such shape-persistent macrocycles. [50][51][52] Continuing interest exists in probing the aromaticity [53] and antiaromaticity of these dehydroannulenes and other macrocyclic p-systems both experimentally and by advanced theoretical calculations. [54][55][56] A new synthetic methodology has been developed to prepare these carbon-rich compounds, adding to the main protocols, which remain oxidative acetylenic coupling to generate buta-1,3-diyne-1,4-diyl fragments [57] and Sonogashira crosscoupling [58,59] to form aryl-acetylenic bonds.…”

Section: Introductionmentioning

confidence: 99%

All‐Carbon Scaffolds by Rational Design

2010

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The search for new molecular and regular polymeric allotropes of carbon has greatly stimulated the preparation and investigation of pi-conjugated acetylenic macrocycles, which often represent substructures of proposed 2D carbon networks. Perethynylated dehydroannulenes, expanded radialenes, and radiaannulenes with large, multi-nanometer-sized all-carbon cores are potent electron acceptors, and their optoelectronic as well as stability and solubility properties are greatly enhanced by peripheral donor substitution. Acetylenic scaffolding into three dimensions has generated an expanded cubane with a C(56) core, the first representative of a new class of "platonic" objects. Exceptional chiroptical properties displayed by enantiomerically pure alleno-acetylenic, shape-persistent macrocycles promise fascinating perspectives for the development of molecular and supramolecular chiroptical materials.

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“…Self-assembled NC framelike arrays are of particular interest due to their unusual optical, electrical, and mechanical properties, as a consequence of the large surface-to-volume ratios that can be attained. These emerging materials offer promise in a broad range of applications including drug delivery and therapeutics (18,(21)(22)(23), novel materials for catalysis (24), optics (18,21), photonics (22,23), and as nanopatterned scaffolds (25,26).…”

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confidence: 99%

Assembly of porous smectic structures formed from interlocking high-symmetry planar nanorings

Avendaño

Jackson

Müller

et al. 2016

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

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Materials comprising porous structures, often in the form of interconnected concave cavities, are typically assembled from convex molecular building blocks. The use of nanoparticles with a characteristic nonconvex shape provides a promising strategy to create new porous materials, an approach that has been recently used with cagelike molecules to form remarkable liquids with "scrabbled" porous cavities. Nonconvex mesogenic building blocks can be engineered to form unique self-assembled open structures with tunable porosity and long-range order that is intermediate between that of isotropic liquids and of crystalline solids. Here we propose the design of highly open liquid-crystalline structures from rigid nanorings with ellipsoidal and polygonal geometry. By exploiting the entropic ordering characteristics of athermal colloidal particles, we demonstrate that high-symmetry nonconvex rings with large internal cavities interlock within a 2D layered structure leading to the formation of distinctive liquid-crystalline smectic phases. We show that these smectic phases possess uniquely high free volumes of up to ∼ 95%, a value significantly larger than the 50% that is typically achievable with smectic phases formed by more conventional convex rod-or disklike mesogenic particles.nanorings | porous liquid crystals | self-assembly S elf-assembly of particles ranging in size from the nanometer to the micrometer scales can be used to fabricate structures in the mesoscale regime (1-5), otherwise difficult to achieve with traditional methods of chemical synthesis. Strategies to produce functional materials from the self-assembly of relatively simple nonspherical (anisotropic) building blocks have undergone unprecedented growth as a result of recent advances in experimental techniques to fashion colloidal and nanoparticles of arbitrary shape and well-defined sizes (6-9). An appealing feature of colloidal particles is that the repulsive and attractive contributions of the interaction between the particles can be modulated by controlling the properties of both the particle surface and the solvent medium to induce different types of forces, including short-range repulsions approaching hard-core (athermal) interactions (10).Colloidal particles are commonly represented using simplified coarse-grained convex geometries including ellipsoids, spherocylinders, polyhedra, and cut spheres (11, 12). The phase behavior of these convex models has been studied extensively by theory and simulation (13,14). Nonconvex (NC) models have received significantly less attention. NC particles offer new possibilities for the fabrication of functional materials as a result of the self-assembly of unique structures driven by interlocking and entanglement (15)(16)(17)(18)(19)(20). As featured in our current paper, NC rings can be packed into exotic highly open (low density) structures. Self-assembled NC framelike arrays are of particular interest due to their unusual optical, electrical, and mechanical properties, as a consequence of the large surface-to-...

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Shape‐Persistent Macrocycles: From Molecules to Materials

Cited by 299 publications

References 76 publications

Polyphenylene‐Based Materials: Control of the Electronic Function by Molecular and Supramolecular Complexity

Polyphenylene‐Based Materials: Control of the Electronic Function by Molecular and Supramolecular Complexity

All‐Carbon Scaffolds by Rational Design

Assembly of porous smectic structures formed from interlocking high-symmetry planar nanorings

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