A Conjugated Polycarbazole Ring around a Porphyrin

Jung, Sung‐Hyun; Pisula, Wojciech; Rouhanipour, Ali; Räder, Hans Joachim; Jacob, Josemon; Müllen, Kläus

doi:10.1002/anie.200601131

Cited by 88 publications

(52 citation statements)

References 29 publications

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“…The latter would provide a kink which, on the one hand, would facilitate ring formation, but, on the other, would interrupt the conjugation. A template-assisted synthesis of a monodisperse fully conjugated 2,7-carbazole-based macrocyclic dodecamer 4 has been reported [57] (Fig. 3).…”

Section: P-conjugated Polyphenylene Macrocyclesmentioning

confidence: 98%

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: 98%

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

2009

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“…Pyrolysis of this binary colloidal structure resulted in an inverse opal with interconnected macropores [12]. Compounds 1 [11], 2 [19], and 3 [17] were synthesized according to procedures described elsewhere. The compounds were dissolved in THF (for 1 and 3) or acetone (for 2) (5-30 mg mL -1 ), and the solution was introduced into the template by drop-casting.…”

Section: Methodsmentioning

confidence: 99%

From Well‐Defined Carbon‐Rich Precursors to Monodisperse Carbon Particles with Hierarchic Structures

et al. 2007

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The creation of nanoscale particles with well-defined structures has long been considered as a promising approach to generate materials with novel properties. Carbonaceous nanoparticles (CNPs) with defined architectures, such as carbon nanotubes (CNTs), C 60 , carbon onions, carbon spheres, and carbon rods are particularly attractive owing to their unique electronic properties and many potential applications.[1] At the same time, when these CNPs are regularly organized, additional functions appear.[2] Such materials are believed to have hierarchic structures, [3] in which the organization of the CNPs forms the first-order structure (FOS) and the configuration of the single CNP forms the second-or higher-order structure (SOS or HOS). Because both the FOS and HOS are responsible for the properties of the bulk material, simple methods to prepare multidimensional carbon materials with hierarchic structures are needed. Template methods are commonly used to produce 3D order in which the silica opal or inverse opal crystals are the most frequently selected templates. [3b,4] Carbonaceous materials have been prepared in these templates by using sucrose or phenolic reactants as precursors, [5] but only amorphous CNPs were obtained. Alternatively, chemical vapor deposition (CVD) over inverse opals was reported to produce crystalline carbons.[4a] Unfortunately, such CVD procedures resulted in inverse carbon opals, not CNPs, and the control over the carbon structures was limited. The preparation of well-defined CNPs with 3D organization is still a challenge owing to the difficulties of controlling molecular interactions at high temperatures. Recent studies on solid-state pyrolysis (SSP) have implied that the structures of CNPs could be controlled by choosing well-defined organometallic precursors. [6][7][8][9] Thus, CNTs were obtained in high yield from SSP of diphenylethyne-metal complexes; [6] while dicobalthexacarbonyl-functionalized poly(p-phenyleneethynylene) afforded carbon-cobalt spheres.[7] Our previous SSP of dendritic polyphenylene-cobalt complexes resulted in uniformly shaped carbon-cobalt nanorods with rectangular cross sections, [8] whereas disclike structures with extended p-systems furnished bamboolike CNTs and carbon shell/metal core cablelike structures. [9] However, in all these experiments, the metal catalysts play a more important role for product formation than the chemical structure of the precursors; and these processes incorporate metals into the pyrolysis products. To prepare metal-free CNPs with defined structures, the design of the precursors requires more attention. Our recent attempts at precursordefined pyrolyses (PDP) produced graphitic nanotubes with brick-walled structures [10] and CNTs with 3D porous-walled structures.[11]

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“…The second requirement has been achieved by the introduction of solubilizing groups to the outside of the carbazole macrocycle (Scheme 1). Unlike the previous conjugated macrocycle developed by us, [7] the design of this new ring, where the long alkyl chains point towards the exterior of the macrocycle and only the four hydroxy anchor groups turn towards the interior, allows a better access for the guest to the cavity.…”

mentioning

confidence: 89%

“…The first requirement has been fulfilled by the synthesis of a 2,7-carbazolediyl-derived macrocycle by using a template-assisted cyclization developed in our laboratory. [7] The target macrocycle contains additional acetylene functions in the backbone, thus allowing the increase in the size of the cavity that is necessary for the introduction of organic molecules. The second requirement has been achieved by the introduction of solubilizing groups to the outside of the carbazole macrocycle (Scheme 1).…”

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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

et al. 2009

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A Conjugated Polycarbazole Ring around a Porphyrin

Cited by 88 publications

References 29 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

From Well‐Defined Carbon‐Rich Precursors to Monodisperse Carbon Particles with Hierarchic Structures

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

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