Filling the Cavity of Conjugated Carbazole Macrocycles with Graphene Molecules: Monolayers Formed by Physisorption Serve as a Surface for Pulsed Laser Deposition

Schmaltz, Bruno; Rouhanipour, Ali; Räder, Hans Joachim; Pisula, Wojciech; Müllen, Kläus

doi:10.1002/anie.200803156

Cited by 70 publications

(47 citation statements)

References 37 publications

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“…The formation of a host-guest complex of the carbazole dodecamer 191 with hexa-peri-hexabenzocoronene (HBC) was reported by Müllen and co-workers (Scheme 30). [143] The two-dimensional supramolecular structures of the host-guest complexes were obtained by physisorption of 191 on HOPG, followed by gas-phase deposition of HBC in a high vacuum. The macrocycle, visible by STM, self-assembled in a hexagonal lattice on HOPG.…”

Section: Carbazole-containing Macrocycles and Related Compoundsmentioning

confidence: 99%

Conjugated Macrocycles: Concepts and Applications

2011

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One of the most important objectives in materials, chemical, and physical sciences is the creation of large conjugated macrocycles with well-defined shapes, since such molecules are not only theoretically and experimentally interesting but also have potential applications in nanotechnology. Fully unsaturated macrocycles are regarded as models for infinitely conjugated π systems with inner cavities, and exhibit unusual optical and magnetic behavior. Macrocycles have interior and exterior sites, and site-specific substitution at both or either site can afford attractive structures, such as 1D, 2D, and 3D supramolecular nanostructures. These nanostructures could be controlled through the use of π-extended large macrocycles by a bottom-up strategy. Numerous shape-persistent π-conjugated macrocycles have been synthesized, but only a few are on the nanoscale. This Review focuses on nanosized π-conjugated macrocycles (>1 nm diameter) and giant macrocycles (>2 nm diameter), and summarizes their syntheses and properties.

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Section: Carbazole-containing Macrocycles and Related Compoundsmentioning

confidence: 99%

Conjugated Macrocycles: Concepts and Applications

2011

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“…Among other supramolecular interactions, host–guest complexation on 2D networks provides an interesting platform to create functional multicomponent layers1011, nanostructures1213 and prototypical devices14, and establish the first step to tailor 3D architectures1516. Furthermore, donor (D) - acceptor (A) complexation of common acceptor molecules into the core of giant macrocycles unveils promising building blocks for the fabrication of complex nanostructures15171819 and self-assembled devices. The design of multifunctional organic materials containing fullerene C 60 as an active component has been extensively investigated in organic electronics2021.…”

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confidence: 99%

Templated bilayer self-assembly of fully conjugated π-expanded macrocyclic oligothiophenes complexed with fullerenes

2017

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Fully conjugated macrocyclic oligothiophenes exhibit a combination of highly attractive structural, optical and electronic properties, and multifunctional molecular thin film architectures thereof are envisioned. However, control over the self-assembly of such systems becomes increasingly challenging, the more complex the target structures are. Here we show a robust self-assembly based on hierarchical non-covalent interactions. A self-assembled monolayer of hydrogen-bonded trimesic acid at the interface between an organic solution and graphite provides host-sites for the epitaxial ordering of Saturn-like complexes of fullerenes with oligothiophene macrocycles in mono- and bilayers. STM tomography verifies the formation of the templated layers. Molecular dynamics simulations corroborate the conformational stability and assign the adsorption sites of the adlayers. Scanning tunnelling spectroscopy determines their rectification characteristics. Current–voltage characteristics reveal the modification of the rectifying properties of the macrocycles by the formation of donor–acceptor complexes in a densely packed all-self-assembled supramolecular nanostructure.

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“…1 Moreover, since macrocycles have both interior and exterior sites, it is anticipated that site speci c interactions between these sites and small molecules or ions will produce interesting supramolecular structures. 5 In accord with these expectations, relatively small shape persistent π conjugated cyclic compounds function as host molecules for fullerenes 6 and inorganic ions.…”

Section: Introductionmentioning

confidence: 74%

Giant Conjugated Macrocycles: Synthesis and Applications

Iyoda

2012

J. Synth. Org. Chem. Jpn.

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Conjugated giant macrocyclic oligothiophenes 2Tn (n 2 4), 5Tn (n 2 6), and 6Tn (n 2 5) composed of 2,5 thienylenes, ethynylenes, and vinylenes with 24π to 180π electron systems have been synthesized using a modi ed McMurry coupling reaction as the key step. For the synthesis of cyclo[n](2,5 thienylene ethynylene)s nCTE (n 10 and 12) composed of 2,5 thienylenes and ethynylenes, a bromination dehydrobromination then double elimination procedure was employed. X ray analyses of 2T2 (24π), 5T2 (60π), and 6T2 (72π) revealed unique molecular and packing structures, re ecting their planar cyclic frameworks having medium to large inner cavities. Interestingly, giant macrocycles self aggregate in the solid state to form various nanostructures re ecting their nanophase separation, and the two photon absorption properties of 6Tn (n 2 5) show that increasing π conjugation leads to an increase in the two photon absorption cross section with magnitudes as high as 100,000 GM being realized. Furthermore, the giant macrocycle 6T5 behaves as a synthetic cyclic pigment comparable to the natural light harvesting system.

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Filling the Cavity of Conjugated Carbazole Macrocycles with Graphene Molecules: Monolayers Formed by Physisorption Serve as a Surface for Pulsed Laser Deposition

Cited by 70 publications

References 37 publications

Conjugated Macrocycles: Concepts and Applications

Conjugated Macrocycles: Concepts and Applications

Templated bilayer self-assembly of fully conjugated π-expanded macrocyclic oligothiophenes complexed with fullerenes

Giant Conjugated Macrocycles: Synthesis and Applications

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